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Journal articles on the topic 'Arylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 19 April 2025

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1

Rossi, Renzo, and Maurizio Ciofalo. "Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art." Current Organic Chemistry 26, no. 3 (February 2022): 215–74. http://dx.doi.org/10.2174/1385272826666220201124008.

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Abstract: This unprecedented review with 322 references provides a critical up-to-date picture of the Pd-catalysed intermolecular direct C–H bond arylation of heteroarenes with arylating reagents alternative to aryl halides that include aryl sulfonates (aryl triflates, tosylates, mesylates, and imidazole-1-sulfonates), diaryliodonium salts, [(diacetoxy)iodo]arenes, arenediazonium salts, 1-aryltriazenes, arylhydrazines and N’-arylhydrazides, arenesulfonyl chlorides, sodium arenesulfinates, arenesulfinic acids, and arenesulfonohydrazides. Particular attention has been paid to summarise the preparation of the various arylating reagents and to highlight the practicality, versatility, and limitations of the various developed arylation protocols, also comparing their results with those achieved in analogous Pd-catalysed arylation reactions involving the use of aryl halides as electrophiles. Mechanistic proposals have also been briefly summarised and discussed. However, data concerning Pd-catalysed direct C–H bond arylations involving the C–H bonds of aryl substituents of the examined heteroarene derivatives have not been taken into account.

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2

Čorić, Ilija, and Jyoti Dhankhar. "Introduction to Spatial Anion Control for Direct C–H Arylation." Synlett 33, no. 06 (February 1, 2022): 503–12. http://dx.doi.org/10.1055/s-0040-1719860.

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AbstractC–H activation of functionally rich molecules without the need for directing groups promises shorter organic syntheses and late-stage diversification of molecules for drug discovery. We highlight recent examples of palladium-catalyzed nondirected functionalization of C–H bonds in arenes as limiting substrates with a focus on the development of the concept of spatial anion control for direct C–H arylation.1 C–H Activation and the CMD Mechanism2 Nondirected C–H Functionalizations of Arenes as Limiting Substrates3 Nondirected C–H Arylation4 Spatial Anion Control for Direct C–H Arylation5 Coordination Chemistry with Spatial Anion Control6 Conclusion

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3

Kalyani, Dipannita. "Pd- and Ni-catalyzed C–H arylations using C–O electrophiles." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 315–19. http://dx.doi.org/10.1515/pac-2014-5033.

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Abstract This manuscript describes the development of Pd- and Ni-catalyzed arylations of unactivated arene C–H bonds using C–O electrophiles. A method for Pd-catalyzed intramolecular C–H arylation is accomplished using inexpensive and readily available tosylates and mesylates as electrophiles. This transformation is efficient for the synthesis of various heterocyclic motifs including furans, carbazoles, indoles, and lactams. Additionally, a protocol for a one-pot sequential tosylation/arylation of phenol derivatives is presented. The use of earth-abundant and inexpensive Ni catalysts for an intramolecular C–H arylation using aryl pivalates as electrophiles is described. Preliminary mechanistic studies for both the Pd- and Ni-catalyzed arylations are discussed.

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4

Bellina, Fabio. "Real Metal-Free C–H Arylation of (Hetero)arenes: The Radical Way." Synthesis 53, no. 15 (March 15, 2021): 2517–44. http://dx.doi.org/10.1055/a-1437-9761.

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AbstractSynthetic methodologies involving the formation of carbon–carbon bonds from carbon–hydrogen bonds are of significant synthetic interest, both for efficiency in terms of atom economy and for their undeniable usefulness in late-stage functionalization approaches. Combining these aspects with being metal-free, the radical C–H intermolecular arylation procedures covered by this review represent both powerful and green methods for the synthesis of (hetero)biaryl systems.1 Introduction2 Arylation with Arenediazonium Salts and Related Derivatives2.1 Ascorbic Acid as the Reductant2.2 Hydrazines as Reductants2.3 Gallic Acid as the Reductant2.4. Polyanilines as Reductants2.5 Chlorpromazine Hydrochloride as the Reductant2.6 Phenalenyl-Based Radicals as Reductants2.7 Electrolytic Reduction of Diazonium Salts2.8 Visible-Light-Mediated Arylation3 Arylation with Arylhydrazines: Generation of Aryl Radicals Using an Oxidant4 Arylation with Diaryliodonium Salts5 Arylation with Aryl Halides6 Conclusions

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5

Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé, and Henri Doucet. "Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations." Beilstein Journal of Organic Chemistry 11 (October 28, 2015): 2012–20. http://dx.doi.org/10.3762/bjoc.11.218.

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We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C–H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp2)–H bonds.

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6

Luo, Anping, Min Zhang, Zhangyi Fu, Jingbo Lan, Di Wu, and Jingsong You. "Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)." Beilstein Journal of Organic Chemistry 16 (March 30, 2020): 530–36. http://dx.doi.org/10.3762/bjoc.16.49.

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The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

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7

Diesendruck, Charles, and Shlomy Arava. "Strategies for the Synthesis of N-Arylammonium Salts." Synthesis 49, no. 16 (June 26, 2017): 3535–45. http://dx.doi.org/10.1055/s-0036-1588868.

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The N-arylation of tertiary amines to provide sp3 quaternary ammonium salts is a challenge in organic chemistry. To date, no general method for such arylations has been established. Here, we summarize a variety of strategies that have been tested, starting with harsh nucleophilic aromatic substitutions, through to the use of copper catalysis and the application of strong electrophiles, such as phenyl cations and benzynes. The achievements and limitations of each method are summarized, and the challenges yet to be met in the synthesis of charged ammonium compounds are described.1 Introduction2 Alkylation of Anilines: The Menshutkin Reaction3 Arylations3.1 Nucleophilic Aromatic Substitutions by Tertiary Amines3.2 Preparation of N-Arylpyridinum Salts from Zincke and Pyrylium Salts3.3 Arylations Using Phenyl Cations3.4 Copper-Catalyzed Arylation of N-Heteroarenes3.5 Benzynes as Aryl Electrophiles4 Conclusions and Perspective

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8

Huang, Qing, Liangxian Liu, Jiayi Zhu, Yu Chen, Feng Lin, and Baoshuang Wang. "Highly Regioselective Arylation of 1,2,3-Triazole N-Oxides with Sodium Arenesulfinates via Palladium-Catalyzed Desulfitative Cross-Coupling Reaction." Synlett 26, no. 08 (March 5, 2015): 1124–30. http://dx.doi.org/10.1055/s-0034-1380186.

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A convenient and highly regioselective palladium-catalyzed direct C5-arylation of 1,2,3-triazole N-oxides was developed in the presence of silver carbonate and tripotassium phosphate. This protocol allowed use of sodium arylsulfinates, diphenylphosphine oxide, and triphenylphosphine as arylating reagents to produce 2-aryl-5-aryl-1,2,3-triazole N-oxides in good to excellent yields, providing a complement to the existing methods for the direct arylation of 1,2,3-triazole N-oxides.

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9

Du, Zhengyin, Hua Feng, Fangli Gang, Yang Che, and Ying Fu. "Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts." Synlett 28, no. 13 (May 4, 2017): 1624–29. http://dx.doi.org/10.1055/s-0036-1588815.

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An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp2 C–H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products with good isolated yields in 24 hours under air atmosphere.

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10

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (March 2, 2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]pyrimidines with o-bromoiodobenzenes.

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11

Maiti, Debabrata, Sumon Basak, and Jyoti Prasad Biswas. "Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents." Synthesis 53, no. 18 (April 19, 2021): 3151–79. http://dx.doi.org/10.1055/a-1485-4666.

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AbstractAryl rings are ubiquitous in the core of numerous natural product and industrially important molecules and thus their facile synthesis is of major interest in the scientific community and industry. Although multiple strategies enable access to these skeletons, metal-catalyzed C–H activation is promising due to its remarkable efficiency. Commercially available organoboron reagents, a prominent arylating partner in the cross-coupling domain, have also been utilized for direct arylation. Organoborons are bench-stable, inexpensive, and readily available coupling partners that promise regioselectivity, chemodivergence, cost-efficiency, and atom-economy without requiring harsh and forcing conditions. This critical, short review presents a summary of all major studies of arylation using organoborons in transition-metal catalysis since 2005.1 Introduction2 Arylation without Directing Group Assistance2.1 Palladium Catalysis2.2 Iron Catalysis2.3 Gold Catalysis3 Arylation with Directing Group Assistance3.1 Palladium Catalysis3.2 Ruthenium Catalysis3.3 Rhodium Catalysis3.4 Nickel Catalysis3.5 Cobalt Catalysis3.6 Copper Catalysis4 Conclusion

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12

Zhou, Yao, Ya Wang, Zhiyi Song, Tamaki Nakano, and Qiuling Song. "Cu-catalyzed C–N bond cleavage of 3-aminoindazoles for the C–H arylation of enamines." Organic Chemistry Frontiers 7, no. 1 (2020): 25–29. http://dx.doi.org/10.1039/c9qo01177c.

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13

Lu, Chaogang, Huawen Huang, Xiaolong Tuo, Pingyu Jiang, Feng Zhang, and Guo-Jun Deng. "Chemoselective metal-free indole arylation with cyclohexanones." Organic Chemistry Frontiers 6, no. 15 (2019): 2738–43. http://dx.doi.org/10.1039/c9qo00603f.

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14

Kepski, Konrad, and Wesley James Moran. "An Unexpected Reaction between Diaryliodonium Salts and DMSO." Organics 3, no. 3 (August 31, 2022): 275–80. http://dx.doi.org/10.3390/org3030020.

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Diaryliodonium salts are useful arylating reagents that have been exploited widely. In this Communication, we demonstrate that heating diphenyliodonium triflate in the solvent DMSO leads to an unexpected arylation reaction. It is postulated that arylation of DMSO at oxygen, followed by a thia-Sommelet–Hauser rearrangement, leads to the formation of 2-thiomethylphenols. More substituted diaryliodonium salts and cyclic diaryliodonium salts are shown to be more stable and less likely to react with DMSO. In conclusion, when using iodonium salts dissolved in DMSO, beware of side-reactions.

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15

Wang, Mei, Wei Wang, Dashan Li, Wen-Jing Wang, Rui Zhan, and Li-Dong Shao. "α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds." Natural Products and Bioprospecting 11, no. 4 (June 7, 2021): 379–404. http://dx.doi.org/10.1007/s13659-021-00312-1.

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Abstractα-C(sp3)-H arylation is an important type of C-H functionalization. Various biologically significant natural products, chemical intermediates, and drugs have been effectively prepared via C-H functionalization. Cyclic carbonyl compounds comprise of cyclic ketones, enones, lactones, and lactams. The α-C(sp3)-H arylation of these compounds have been exhibited high efficiency in forming C(sp3)-C(sp2) bonds, played a crucial role in organic synthesis, and attracted majority of interests from organic and medicinal communities. This review focused on the most significant advances including methods, mechanism, and applications in total synthesis of natural products in the field of α-C(sp3)-H arylations of cyclic carbonyl compounds in recent years.

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16

Fischer, Carolin, and Burkhard Koenig. "Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds." Beilstein Journal of Organic Chemistry 7 (January 14, 2011): 59–74. http://dx.doi.org/10.3762/bjoc.7.10.

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N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald–Hartwig-type reactions, copper-mediated Ullmann-type and Chan–Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan–Lam reactions. Chan–Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald–Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C–N bond formation in the course of a total synthesis or drug synthesis.

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17

Yamaguchi, Junichiro, Ryota Isshiki, Ryosuke Takise, Kenichiro Itami, and Kei Muto. "Catalytic α-Arylation of Ketones with Heteroaromatic Esters." Synlett 28, no. 19 (October 23, 2017): 2599–603. http://dx.doi.org/10.1055/s-0036-1589120.

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Heteroaromatic esters were found to be applicable as an arylating agent for the Pd-catalyzed α-arylation of ketones in a decarbonylative fashion. The use of our in-house ligand, dcypt, enabled this unique bond formation. Considering the ubiquity and low cost of aromatic esters, the present work will allow for rapid access to valuable α-aryl carbonyl compounds.

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18

Vásquez-Céspedes, Suhelen, Michael Holtkamp, Uwe Karst, and Frank Glorius. "Reusable and Magnetic Palladium and Copper Oxide Catalysts in Direct ortho and meta Arylation of Anilide Derivatives." Synlett 28, no. 20 (May 2, 2017): 2759–64. http://dx.doi.org/10.1055/s-0036-1589007.

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We report a general, direct C–H arylation of anilide derivatives using reusable palladium or copper oxide on magnetite as heterogeneous precatalysts. Highly selective ortho and meta arylations are achieved using electronically and sterically diverse diaryliodonium salts. Catalytically active soluble species from the heterogeneous precursors were detected by experimental techniques. Preliminary mechanistic investigation suggests different reaction pathways for each of the catalysts.

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19

Gao, Ke, Keita Yamamoto, Keisuke Nogi, and Hideki Yorimitsu. "Palladium-Catalyzed Arylation of Benzylic C–H Bonds of Azaarylmethanes with Aryl Sulfides." Synlett 28, no. 20 (August 17, 2017): 2956–60. http://dx.doi.org/10.1055/s-0036-1589098.

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Benzylic C–H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.

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20

Paul, Sayantan, and Asish K. Bhattacharya. "Hydroxyl directed C-arylation: synthesis of 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones under transition-metal free conditions." Organic & Biomolecular Chemistry 16, no. 3 (2018): 444–51. http://dx.doi.org/10.1039/c7ob01929g.

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Hydroxyl assisted, efficient, transition-metal free and direct C-arylation of 3-hydroxychromone and 5-hydroxy pyran-4-one moieties in the presence of a base, air as an oxidant and arylhydrazines as arylating agents to furnish highly biologically active 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones has been developed.

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21

Huang, Hai-Yun, Haoran Li, Thierry Roisnel, Jean-François Soulé, and Henri Doucet. "Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives." Beilstein Journal of Organic Chemistry 15 (August 29, 2019): 2069–75. http://dx.doi.org/10.3762/bjoc.15.204.

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The Pd-catalyzed C–H bond functionalization of lilolidine was investigated. The use of a palladium-diphosphine catalyst associated to acetate bases in DMA was found to promote the regioselective arylation at α-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these α-arylated lilolidines, a second arylation at the β-position gives the access to α,β-diarylated lilolidines containing two different aryl groups. The one pot access to α,β-diarylated lilolidines with two identical aryl groups is also possible by using a larger amount of aryl bromide. The synthesis of 5,6-dihydrodibenzo[a,c]pyrido[3,2,1-jk]carbazoles from lilolidine via three successive direct arylations is also described. Therefore, this methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C–H bond functionalization steps allowing to tune their biological properties.

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22

Mamgain, Ritu, Kokila Sakthivel, and Fateh V. Singh. "Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts." Beilstein Journal of Organic Chemistry 20 (November 13, 2024): 2891–920. http://dx.doi.org/10.3762/bjoc.20.243.

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Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these salts serve as effective electrophilic arylating reagents in various organic syntheses. The use of diaryliodoniums in C–C and carbon–heteroatom bond formations, particularly under metal-free conditions, has further enhanced the popularity of these reagents. In this review, we concentrate on various arylation reactions involving carbon and other heteroatoms, encompassing rearrangement reactions in the absence of any metal catalyst, and summarize advancements made in the last five years.

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23

Jeyachandran, Rajkumar, Harish Kumar Potukuchi, and Lutz Ackermann. "Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles." Beilstein Journal of Organic Chemistry 8 (October 16, 2012): 1771–77. http://dx.doi.org/10.3762/bjoc.8.202.

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Step-economical syntheses of annulated 1,2,3-triazoles were accomplished through copper-catalyzed intramolecular direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide–alkyne cycloadditions (CuAAC) and C–H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regioselectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C–H/N–H arylation reaction.

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24

Rosadoni, Elisabetta, Federico Banchini, Sara Bellini, Marco Lessi, Luca Pasquinelli, and Fabio Bellina. "Ligandless Palladium-Catalyzed Direct C-5 Arylation of Azoles Promoted by Benzoic Acid in Anisole." Molecules 27, no. 23 (December 2, 2022): 8454. http://dx.doi.org/10.3390/molecules27238454.

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The palladium-catalyzed direct arylation of azoles with (hetero)aryl halides is nowadays one of the most versatile and efficient procedures for the selective synthesis of heterobiaryls. Although this procedure is, due to its characteristics, also of great interest in the industrial field, the wide use of a reaction medium such as DMF or DMA, two polar aprotic solvents coded as dangerous according to environmental, health, safety (EHS) parameters, strongly limits its actual use. In contrast, the use of aromatic solvents as the reaction medium for direct arylations, although some of them show good EHS values, is poorly reported, probably due to their low solvent power against reagents and their potential involvement in undesired side reactions. In this paper we report an unprecedented selective C-5 arylation procedure involving anisole as an EHS green reaction solvent. In addition, the beneficial role of benzoic acid as an additive was also highlighted, a role that had never been previously described.

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25

Zhou, Lijing, Hongji Li, Wenge Zhang, and Lei Wang. "Tuning chemoselectivity in O-/N-arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates via aryne insertion." Chemical Communications 54, no. 38 (2018): 4822–25. http://dx.doi.org/10.1039/c8cc00124c.

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A finely tunable chemoselectivity in arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates is reported, including silver-catalysed O-arylation and metal-free N-arylation.

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26

Zheng, Peng-Fei, Yang An, Zuo-Yi Jiao, Zhou-Bao Shi, and Fu-Min Zhang. "Comprehension of the α-Arylation of Nitroalkanes." Current Organic Chemistry 23, no. 14 (October 16, 2019): 1560–80. http://dx.doi.org/10.2174/1385272823666190820113718.

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Background: α-Aryl substituted nitroalkanes are important synthetic intermediates for the preparation of pharmaceutical molecules, natural products, and functional materials. Due to their scare existence in Nature, synthesis of these compounds has attracted the attention of synthetic and medicinal chemists, rendering α-arylation of nitroalkanes of an important research topic. This article summarizes the important advances of α- arylation of nitroalkanes since 1963. Results: After a brief introduction of the synthetic application and the reactions of nitroalkanes, this article reviewed the synthetic methods for the α-arylated aliphatic nitro compound. The amount of research on α-arylation of nitroalkanes using various arylation reagents and the discovery of elegant synthetic approaches towards such skeleton have been discussed. This review described these advances in two sections. One is the arylation of non-activated nitroalkanes, with an emphasis on the application of diverse arylation reagents; the other focuses on the arylation of activated nitroalkanes, including dinitroalkanes, trinitroalkanes, α-nitrosulfones, α-nitroesters, α-nitrotoluenes, and α-nitroketones. The synthetic application of these methods has also been presented in some cases. Conclusion: In this review, we described the progress of α-arylation of nitroalkanes. Although the immense amount of research on α-arylation of aliphatic nitro compounds has been achieved, many potential issues still need to be addressed, especially the asymmetric transformation and its wide application in organic synthesis.

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27

Zhang, Huaiyuan, Ke-Hu Wang, Junjiao Wang, Yingpeng Su, Danfeng Huang, and Yulai Hu. "N-Arylations of trifluoromethylated N-acylhydrazones with diaryliodonium salts as arylation reagents." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2940–47. http://dx.doi.org/10.1039/c9ob00236g.

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A novel and efficient N-arylation of trifluoromethylated N-acylhydrazones is described by using diaryliodonium salts as arylation reagents in the presence of copper salts. A wide variety of N-aryl acylhydrazones are obtained with good to excellent yields under mild reaction conditions.

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28

Mastalir, Ágnes, and Árpád Molnár. "On the Current Status of Ullmann-Type N-Arylation Reactions Promoted by Heterogeneous Catalysts." Inorganics 11, no. 7 (June 27, 2023): 276. http://dx.doi.org/10.3390/inorganics11070276.

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Ullmann-type C–N heterocoupling reactions have been applied for the syntheses of N-arylated amines. In the past decade, transition metal-catalyzed N-arylations have been recognized as particularly efficient procedures for the preparation of nitrogen-containing aromatic systems. These reactions typically carried out under optimized conditions, have also been found to be suitable for the synthesis of complex molecules with other functional groups, including natural products, drugs, or pharmaceuticals. Most importantly, copper-catalyzed N-arylations have been studied and employed in the total synthesis of biologically active compounds. The construction of fused N-heterocyclic compounds also remained the subject of extensive research because of their potential applications in drug discovery and the development of functional materials. The aim of this review is to summarize the recent progress in the synthetic applications of Ullmann-type N-arylation reactions performed in heterogeneous systems. In particular, the utilization of copper and palladium species immobilized on various support materials, modified by surface functionalization, has been discussed and evaluated.

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29

Wencel-Delord, Joanna, and Françoise Colobert. "Challenging Atroposelective C–H Arylation." SynOpen 04, no. 04 (October 2020): 107–15. http://dx.doi.org/10.1055/s-0040-1705981.

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AbstractAtropisomeric molecules are privileged scaffolds, not only as ligands for asymmetric synthesis, but also as biologically active products and advanced materials. Although very attractive from a sustainability viewpoint, the direct construction of the stereogenic axis through asymmetric C–H arylation is very challenging and consequently only a few examples have been reported. This short review summarizes these very recent results on the atropo-enantio or diastereoselective synthesis of atropisomeric (hetero)biaryl molecules; transformations during which the Ar–Ar atropisomeric axis is formed during the C–H activation process.1 Introduction2 Atropo-enantioselective Intermolecular Pd-Catalyzed C–H Arylation of Thiophene Derivatives3 Atropodiastereoselective Intermolecular Pd-Catalyzed C–H Arylation towards Terphenyl Scaffolds Bearing Two Atropisomeric Axes4 Atropo-enantioselective Intramolecular Pd-Catalyzed C–H Arylation towards Atropisomeric Benzodiazepinones5 Atropo-enantioselective Intermolecular Pd-Catalyzed C–H Arylation of Heteroarenes6 Rh-Catalyzed Atropo-enantioselective C–H Arylation of Diazonaphthoquinones7 Conclusion

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30

Sun, Chu-Han, Yi Lu, Qing Zhang, Rong Lu, Lin-Qing Bao, Mei-Hua Shen, and Hua-Dong Xu. "Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones." Organic & Biomolecular Chemistry 15, no. 19 (2017): 4058–63. http://dx.doi.org/10.1039/c7ob00040e.

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31

Mayhugh, Amy L., and Christine K. Luscombe. "Room-temperature Pd/Ag direct arylation enabled by a radical pathway." Beilstein Journal of Organic Chemistry 16 (March 13, 2020): 384–90. http://dx.doi.org/10.3762/bjoc.16.36.

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Direct arylation is an appealing method for preparing π-conjugated materials, avoiding the prefunctionalization required for traditional cross-coupling methods. A major effort in organic electronic materials development is improving the environmental and economic impact of production; direct arylation polymerization (DArP) is an effective method to achieve these goals. Room-temperature polymerization would further improve the cost and energy efficiencies required to prepare these materials. Reported herein is new mechanistic work studying the underlying mechanism of room temperature direct arylation between iodobenzene and indole. Results indicate that room-temperature, Pd/Ag-catalyzed direct arylation systems are radical-mediated. This is in contrast to the commonly proposed two-electron mechanisms for direct arylation and appears to extend to other substrates such as benzo[b]thiophene and pentafluorobenzene.

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32

Urgoitia, Garazi, Maria Teresa Herrero, Fátima Churruca, Nerea Conde, and Raul SanMartin. "Direct Arylation in the Presence of Palladium Pincer Complexes." Molecules 26, no. 14 (July 20, 2021): 4385. http://dx.doi.org/10.3390/molecules26144385.

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Direct arylation is an atom-economical alternative to more established procedures such as Stille, Suzuki or Negishi arylation reactions. In comparison with other palladium sources and ligands, the use of palladium pincer complexes as catalysts or pre-catalysts for direct arylation has resulted in improved efficiency, higher reaction yields, and advantageous reaction conditions. In addition to a revision of the literature concerning intra- and intermolecular direct arylation reactions performed in the presence of palladium pincer complexes, the role of these remarkably active catalysts will also be discussed.

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Peng, Jing, Chao Chen, and Chanjuan Xi. "β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst." Chem. Sci. 7, no. 2 (2016): 1383–87. http://dx.doi.org/10.1039/c5sc03903g.

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34

Zhang, Tao, Zi-Yu Zhang, Guowei Kang, Tao Sheng, Jie-Lun Yan, Yuan-Bin Yang, Yuxin Ouyang, and Jin-Quan Yu. "Enantioselective remote methylene C−H (hetero)arylation of cycloalkane carboxylic acids." Science 384, no. 6697 (May 17, 2024): 793–98. http://dx.doi.org/10.1126/science.ado1246.

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Stereoselective construction of γ- and δ-stereocenters in carbonyl compounds is a pivotal objective in asymmetric synthesis. Here, we report chiral bifunctional oxazoline-pyridone ligands that enable enantioselective palladium-catalyzed remote γ-C−H (hetero)arylations of free cycloalkane carboxylic acids, which are essential carbocyclic building blocks in organic synthesis. The reaction establishes γ-tertiary and α-quaternary stereocenters simultaneously in up to >99% enantiomeric excess, providing access to a wide range of cyclic chiral synthons and bioactive molecules. The sequential enantioselective editing of two methylene C–H bonds can be achieved by using chiral ligands with opposite configuration to construct carbocycles containing three chiral centers. Enantioselective remote δ-C−H (hetero)arylation is also realized to establish δ-stereocenters that are particularly challenging to access using classical methodologies.

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Haddad, Nizar, Chris Senanayake, Hari Mangunuru, Christian Malapit, Jonathan Reeves, Bo Qu, Sonia Rodriguez, et al. "Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands." Synthesis 50, no. 22 (June 28, 2018): 4435–43. http://dx.doi.org/10.1055/s-0036-1591590.

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The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me2-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd2(dba)3/i-Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me2-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

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36

Liu, Zhengfen, Minyan Li, Bijun Wang, Guogang Deng, Wen Chen, Byeong-Seon Kim, Hongbin Zhang, Xiaodong Yang, and Patrick J. Walsh. "Chemoselective synthesis of aryl(pyridinyl)methanol derivatives through Ni-NIXANTPHOS catalyzed α-arylation and tandem arylation/rearrangement of pyridylmethyl ethers." Organic Chemistry Frontiers 5, no. 12 (2018): 1870–76. http://dx.doi.org/10.1039/c8qo00207j.

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Kobiki, Yohsuke, Shin-ichi Kawaguchi, Takashi Ohe, and Akiya Ogawa. "Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides." Beilstein Journal of Organic Chemistry 9 (June 13, 2013): 1141–47. http://dx.doi.org/10.3762/bjoc.9.127.

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A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.

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38

DRAHL, CARMEN. "ENLIGHTENING ARYLATION." Chemical & Engineering News Archive 89, no. 45 (November 7, 2011): 10. http://dx.doi.org/10.1021/cen-v089n045.p010a.

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39

Li, Dengke, Ning Xu, Yicheng Zhang, and Lei Wang. "A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides." Chem. Commun. 50, no. 94 (2014): 14862–65. http://dx.doi.org/10.1039/c4cc06457g.

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40

Zhang, Jingchang, Qingwen Liu, Xufei Liu, Suoqin Zhang, Pingping Jiang, Yanxiang Wang, Shengyuan Luo, Yang Li, and Qifeng Wang. "Palladium(ii)-catalyzed meta-selective direct arylation of O-β-naphthyl carbamate." Chemical Communications 51, no. 7 (2015): 1297–300. http://dx.doi.org/10.1039/c4cc07997c.

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41

Besson, Thierry, and Corinne Fruit. "Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts." Pharmaceuticals 14, no. 7 (July 11, 2021): 661. http://dx.doi.org/10.3390/ph14070661.

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Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

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Wen, Li-Rong, Qiang-Yu Shen, Wei-Si Guo, and Ming Li. "Copper-catalyzed tandem arylation–cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2,3-b]indoles." Organic Chemistry Frontiers 3, no. 7 (2016): 870–74. http://dx.doi.org/10.1039/c6qo00133e.

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A Cu-catalyzed arylation–cyclization approach is developed for the synthesis of thiochromeno[2,3-b]indoles through the S-arylation, 5-endo-trig cyclization, and Friedel–Crafts-type cyclization sequence.

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Oeser, Petr, Jakub Koudelka, Artem Petrenko, and Tomáš Tobrman. "Recent Progress Concerning the N-Arylation of Indoles." Molecules 26, no. 16 (August 22, 2021): 5079. http://dx.doi.org/10.3390/molecules26165079.

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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Koizumi, Yu, Kento Taniguchi, Xiongjie Jin, Kazuya Yamaguchi, Kyoko Nozaki, and Noritaka Mizuno. "Formal arylation of NH3 to produce diphenylamines over supported Pd catalysts." Chemical Communications 53, no. 78 (2017): 10827–30. http://dx.doi.org/10.1039/c7cc06737b.

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In the presence of Pd/Al₂O₃, various diphenylamines could be synthesized through acceptorless formal arylation using urea as a nitrogen source and cyclohexanones as arylation sources.

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45

Prajapati, D., C. Schulzke, M. K. Kindermann, and A. R. Kapdi. "Selective palladium-catalysed arylation of 2,6-dibromopyridine using N-heterocyclic carbene ligands." RSC Advances 5, no. 65 (2015): 53073–85. http://dx.doi.org/10.1039/c5ra10561g.

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A selective palladium-catalysed arylation of 2,6-dibromopyridine has been developed by employing N-heterocyclic carbene ligands. Selective mono-arylation was performed in water/acetonitrile solvent at ambient temperature and low catalyst loading.

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46

Al-Zoubi, Raed M., Walid K. Al-Jammal, Michael J. Ferguson, and Graham K. Murphy. "Domino C–C/C–O bond formation: palladium-catalyzed regioselective synthesis of 7-iodobenzo[b]furans using 1,2,3-triiodobenzenes and benzylketones." RSC Advances 11, no. 48 (2021): 30069–77. http://dx.doi.org/10.1039/d1ra05730h.

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A facile and unprecedented synthesis of 7-iodobenzo[b]furans via a highly regioselective tandem α-arylation/intramolecular O-arylation is reported that is efficient, scalable and creates versatile precursors for further chemical manipulation.

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47

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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48

Malins, Lara R. "Transition Metal-Promoted Arylation: An Emerging Strategy for Protein Bioconjugation." Australian Journal of Chemistry 69, no. 12 (2016): 1360. http://dx.doi.org/10.1071/ch16416.

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Transition metal-mediated arylation chemistry is emerging as a powerful tool for the selective modification of native peptides and proteins, providing new opportunities in the field of bioconjugation. This highlight paper will summarize recent methodologies for the regio- and chemoselective arylation of select proteinogenic side chains and backbone amide N–H bonds within unprotected peptides and proteins. The importance of the metal–ligand complex in achieving tunable selectivity and the inherent benefits of arylation as a mode of covalent protein modification will be highlighted.

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Babu, Srinivasarao Arulananda, and Arup Dalal. "Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs." Synthesis 53, no. 18 (March 31, 2021): 3307–24. http://dx.doi.org/10.1055/a-1472-0881.

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AbstractWe report the application of the Pd(II)-catalyzed, directing-group-aided C–H arylation/alkylation tactics to functionalize the pyrene core, especially, the relatively inaccessible C2 and K-region C10 positions of the pyrene core and augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene motifs. The Pd(II)-catalyzed β-C–H arylation/alkylation of the C2-position of pyrene-1-carboxamide possessing an 8-aminoquinoline directing group yielded various C1,C2-disubstituted pyrenes. Similarly, the Pd(II)-catalyzed selective γ-C–H arylation/alkylation of the C10-position of N-(pyren-1-yl)picolinamide, possessing a picolinamide directing group, yielded various C1,C10-disubstituted pyrenes. Examples of C(9)–H arylation of pyrene-1-carboxamide and the removal of the directing group after the C–H arylation/alkylation reactions were also shown. The structures of representative pyrene derivatives were confirmed by the X-ray structure analysis. Given the importance of the pyrene derivatives in various fields of chemical sciences, this report is a contribution towards augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene amide motifs.

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Uçar, Sefa, and Arif Daştan. "Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes." Synthesis, July 2, 2021. http://dx.doi.org/10.1055/a-1543-3743.

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AbstractTransition-metal-free arylation reactions have attracted considerable attention for economic and environmental reasons over the past 40 years. In recent years, much effort has been made to develop efficient transition-metal-free approaches for the arylation of heteroarenes. Covering the literature from 2015 to early 2021, this review aims to provide a thorough overview of the synthetic and mechanistic aspects of these atom-economical and environmentally benign reactions.1 Introduction2 Arylation of Pre-functionalized Heteroarenes2.1 Arylation of Heteroaryl Halides2.2 Decarboxylative Arylation of Heteroarenes3 Direct C–H Arylation of Heteroarenes3.1 C(sp2)–H Arylation3.2 C(sp3)–H Arylation4 N-Arylation of Heteroarenes5 Summary and Outlook

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