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Journal articles on the topic 'C-H Arylation Reactions'

Author: Grafiati

Published: 6 September 2023

Last updated: 31 July 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 (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 prepa

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2

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 (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]

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3

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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4

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (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, trem

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5

Dhankhar, Jyoti, and Ilija Čorić. "Direct C–H Arylation." CHIMIA 76, no. 9 (2022): 777. http://dx.doi.org/10.2533/chimia.2022.777.

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Bonds between hydrogen and carbon atoms are the most frequent type of bonds in organic molecules. The ability to replace hydrogen atoms by making other types of bonds to carbon atoms can enable simpler access to complex organic molecules by substituting multistep synthetic sequences. The use of transition metal catalysts to activate C–H bonds is particularly attractive as it offers control over the reactivity and selectivity through catalyst design. However, such functionalization includes the difficult breaking of strong C–H bonds that are not activated by the presence of other groups. Additi

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6

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (2020): 2311–29. http://dx.doi.org/10.1055/s-0040-1707115.

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Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and

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7

Terai, Seiya, Yuki Sato, Takuya Kochi, and Fumitoshi Kakiuchi. "Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives." Beilstein Journal of Organic Chemistry 16 (March 31, 2020): 544–50. http://dx.doi.org/10.3762/bjoc.16.51.

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An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-positions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C–H and C–O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[a,d,j,m]coronenes in short steps from readily available starting materials. Tetrabenzo[a,d,j,m]coronenes possessing two different types of substituents were obtained selectively by s

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8

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 (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 heteroc

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9

Ngo, Thang Ngoc, Peter Ehlers, Tuan Thanh Dang, Alexander Villinger, and Peter Langer. "Synthesis of indolo[1,2-f]phenanthridines by Pd-catalyzed domino C–N coupling/hydroamination/C–H arylation reactions." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3321–30. http://dx.doi.org/10.1039/c5ob00013k.

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10

Keske, Eric C., Brandon D. Moore, Olena V. Zenkina, Ruiyao Wang, Gabriele Schatte, and Cathleen M. Crudden. "Highly selective directed arylation reactions via back-to-back dehydrogenative C–H borylation/arylation reactions." Chem. Commun. 50, no. 69 (2014): 9883–86. http://dx.doi.org/10.1039/c4cc02499k.

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11

Gao, Pin, Yu-Rui Gu, and Xin-Hua Duan. "Direct C–H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C–C Bonds Formation." Synthesis 49, no. 15 (2017): 3407–21. http://dx.doi.org/10.1055/s-0036-1588493.

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Aromatic heterocycles are an important class of compounds found in a wide range of natural products, pharmaceutically active molecules and organic materials. Recently, the direct radical functionalization of heteroaromatic C–H bonds has become an efficient and attractive method to access substituted heteroarenes. Especially, redox-neutral radical reactions have attracted much attention of chemists due to their potential advantages such as mild conditions, free of external oxidants, and good functional group tolerance. So far, a series of redox-neutral radical reactions have been developed. In

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12

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (2020): 634. http://dx.doi.org/10.3390/catal10060634.

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient an

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13

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 (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 th

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14

Kónya, Krisztina, and Zoltán Sipos. "Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C–H Activation." Synthesis 50, no. 08 (2018): 1610–20. http://dx.doi.org/10.1055/s-0036-1591773.

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A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.

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15

Yemene, Amsalu Efrem, Vishwesh Venkatraman, David Moe Almenningen, Bård Helge Hoff, and Odd Reidar Gautun. "Synthesis of Novel 3,6-Dithienyl Diketopyrrolopyrrole Dyes by Direct C-H Arylation." Molecules 25, no. 10 (2020): 2349. http://dx.doi.org/10.3390/molecules25102349.

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Direct C-H arylation coupling is potentially a more economical and sustainable process than conventional cross-coupling. However, this method has found limited application in the synthesis of organic dyes for dye-sensitized solar cells. Although direct C-H arylation is not an universal solution to any cross-coupling reactions, it efficiently complements conventional sp2−sp2 bond formation and can provide shorter and more efficient routes to diketopyrrolopyrrole dyes. Here, we have applied palladium catalyzed direct C-H arylation in the synthesis of five new 3,6-dithienyl diketopyrrolopyrrole d

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16

Zozik, Yunus, Melike Sevim, Ferruh Lafzi, Haydar Kilic, and Önder Metin. "Magnetically recoverable nickel-palladium alloy nanocatalysts for direct C–H arylation reactions." Dalton Transactions 50, no. 47 (2021): 17515–23. http://dx.doi.org/10.1039/d1dt02985a.

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Magnetically recoverable bimetallic NiPd alloy nanocatalysts were fabricated for the C–H arylation of heteroarenes with aryl halides. The nanocatalysts showed very good performance and the biaryl products were obtained in good to excellent yields.

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17

Wang, Shoufeng, Shuya Xing, Yingying Zhang та ін. "The Ag-promoted α-C–H arylation of alcohols". RSC Advances 9, № 71 (2019): 41847–50. http://dx.doi.org/10.1039/c9ra09954a.

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18

Fujiwara, Yuzo, and Chengguo Jia. "New developments in transition metal-catalyzed synthetic reactions via C-H bond activation." Pure and Applied Chemistry 73, no. 2 (2001): 319–24. http://dx.doi.org/10.1351/pac200173020319.

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Several novel and useful reactions involving transition metal-catalyzed C-H bond activation discovered in our laboratory have been summarized here, which includes olefin arylation, hydroarylation of alkynes, carboxylation of arenes and alkanes, and acetoxylation and aminomethylation of alkanes. Possible mechanisms of these reactions have been suggested.

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19

Snieckus, Victor, Livia da Frota, Cédric Schneider, Mauro de Amorim, and Alcides da Silva. "Chemoselective Ruthenium-Catalyzed C–O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones." Synlett 28, no. 19 (2017): 2587–93. http://dx.doi.org/10.1055/s-0036-1590985.

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Ruthenium-catalyzed C–O bond activation/arylation of methoxy and O-carbamoyl-substituted fluorenones is reported. Established are new reactions of compound 1 (X = H) to aryl (2) and 1,8-diaryl (3) fluorenones. Orthogonal ruthenium-, palladium- and nickel-catalyzed reactions with Suzuki–Miyaura reactions to afford 1,4-diaryl (4) and 1,4,8-triaryl fluorenones (5) are also described. The ready availability of starting methoxy fluorenones by directed ortho and remote metalation tactics confers facility to the presented reactions which may find application in material science areas. DFT calculation

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20

Liu, Yunyun, Yi Zhang, Meiying Huang, and Jie-Ping Wan. "Step economical synthesis of o-aryl benzamides via C–H activation relayed by the in situ installation of directing group: a multicomponent method." RSC Advances 5, no. 57 (2015): 46192–96. http://dx.doi.org/10.1039/c5ra09078d.

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Multicomponent reactions have been successfully applied as a platform for the step economical C–H activation based synthesis wherein the in situ installation of directing group and the subsequent C–H arylation have been achieved in one-step.

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21

Fukuyama, Takahide, Md Taifur Rahman, Hiroshi Mashima, Hideo Takahashi, and Ilhyong Ryu. "Ionic liquids are not innocent in Pd catalysis. C–H arylation of thiazolium and imidazolium ionic liquids with aryl halides." Organic Chemistry Frontiers 4, no. 9 (2017): 1863–66. http://dx.doi.org/10.1039/c7qo00331e.

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The ionic liquids bearing an aromatic vinylic C–H moiety are not innocent during Pd-catalyzed cross-coupling reactions of aryl halides. Palladium-catalyzed direct C–H arylation of thiazolium and imidazolium ionic liquids took place to give arylated ionic liquids.

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22

Keske, Eric C., Brandon D. Moore, Olena V. Zenkina, Ruiyao Wang, Gabriele Schatte, and Cathleen M. Crudden. "ChemInform Abstract: Highly Selective Directed Arylation Reactions via Back-to-Back Dehydrogenative C-H Borylation/Arylation Reactions." ChemInform 46, no. 4 (2015): no. http://dx.doi.org/10.1002/chin.201504198.

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23

Shchegolkov, Evgeny V., Yanina V. Burgart, Daria A. Matsneva, et al. "Polyfluoroalkylated antipyrines in Pd-catalyzed transformations." RSC Advances 11, no. 56 (2021): 35174–81. http://dx.doi.org/10.1039/d1ra06967e.

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24

Yang, Zhenzhen, Zhenghui Liu, Hongye Zhang, et al. "N-Doped porous carbon nanotubes: synthesis and application in catalysis." Chemical Communications 53, no. 5 (2017): 929–32. http://dx.doi.org/10.1039/c6cc09374d.

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25

McIntyre, Jamie, Irene Mayoral-Soler, Pedro Salvador, Albert Poater, and David J. Nelson. "Insights into mechanism and selectivity in ruthenium(ii)-catalysed ortho-arylation reactions directed by Lewis basic groups." Catalysis Science & Technology 8, no. 12 (2018): 3174–82. http://dx.doi.org/10.1039/c8cy00592c.

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26

Chang, Yu-Chieh, Kun-Mu Lee, Chang-Chieh Ting, and Ching-Yuan Liu. "Step-efficient access to new starburst hole-transport materials with carbazole end-groups for perovskite solar cells via direct C–H/C–Br coupling reactions." Materials Chemistry Frontiers 3, no. 10 (2019): 2041–45. http://dx.doi.org/10.1039/c9qm00309f.

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27

Wang, Liang, Jun Shen, Sen Yang, Wenjie Liu, Qun Chen, and Mingyang He. "C–H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium." Green Chemistry 20, no. 6 (2018): 1290–96. http://dx.doi.org/10.1039/c8gc00012c.

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28

Zhou, Chun-Ni, Zi-Ang Zheng, George Chang, et al. "Phosphorus-Containing Groups Assisted Transition Metal Catalyzed C-H Activation Reactions." Current Organic Chemistry 23, no. 2 (2019): 103–35. http://dx.doi.org/10.2174/1385272823666190213113059.

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Over the last few decades, transition metal-catalyzed direct C-H activation with the assistance of a coordinating directing group has emerged as an atom- and stepeconomical synthetic tools to transform C–H bonds into carbon-carbon or carbonheteroatom bonds. Although the strategies involving regioselective C–H cleavage assisted by various directing groups have been extensively reviewed in the literature, we now attempt to give an overview of the recent advances on phosphorus-containing functional group assisted C-H activation reactions catalyzed by transition-metal catalysts including mechanist

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29

Tanji, Yutaka, Ryo Hamaguchi, Yasushi Tsuji, and Tetsuaki Fujihara. "Pd-Catalyzed intermolecular C–H bond arylation reactions: effect of bulkiness of carboxylate ligands." Chemical Communications 56, no. 27 (2020): 3843–46. http://dx.doi.org/10.1039/d0cc01129k.

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A bulky carboxylic acid bearing one 1-adamantylmethyl and two methyl substituents at the α-position is demonstrated to work as an efficient carboxylate ligand source in Pd-catalyzed intermolecular C(sp<sup>2</sup>)–H bond arylation reactions.

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30

Kündig, E. Peter, Yixia Jia, Dmitry Katayev, and Masafumi Nakanishi. "Asymmetric Pd-NHC*-catalyzed coupling reactions." Pure and Applied Chemistry 84, no. 8 (2012): 1741–48. http://dx.doi.org/10.1351/pac-con-12-02-10.

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Very high asymmetric inductions result in the Pd-catalyzed intramolecular arylation of amides to give 3,3-disubstituted oxindoles when new in situ-generated chiral N-heterocyclic carbene (NHC*) ligands are employed. Structural studies show that conformational locking to minimize allylic strain is the key to understanding the function of these ligands. New applications of these ligands in the frontier area of asymmetric coupling reactions involving C(sp3)–H bonds are detailed. Highly enantioenriched fused indolines are accessible using either preformed- or in situ-generated Pd-NHC* catalysts. R

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31

Brodnik, Helena, Franc Požgan, and Bogdan Štefane. "Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions." Organic & Biomolecular Chemistry 14, no. 6 (2016): 1969–81. http://dx.doi.org/10.1039/c5ob02364e.

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32

Shen, Rui, Wei Zhu, Xiaodong Yan, et al. "A porphyrin porous organic polymer with bicatalytic sites for highly efficient one-pot tandem catalysis." Chemical Communications 55, no. 6 (2019): 822–25. http://dx.doi.org/10.1039/c8cc08918c.

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A porphyrin-based porous organic polymer with bifunctional catalytic sites was synthesized, and exhibits high stability and excellent catalytic efficiency for tandem catalytic reactions of C–H arylation and Suzuki coupling.

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33

Patil, Mahendra. "Mechanism of the t-BuOM (M = K, Na, Li)/DMEDA-Mediated Direct C–H Arylation of Benzene: A Computational Study." Synthesis 52, no. 19 (2020): 2883–91. http://dx.doi.org/10.1055/s-0040-1707882.

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Over the past ten years, a combination of organic additive and t-BuOK/t-BuONa has been successfully used for the direct C–H arylation of arenes. Conceptually different from transition-metal-catalyzed cross-coupling reactions, these t-BuOK-mediated reactions have raised significant curiosity among organic chemists. Herein, a systematic computational study of each elementary step of the t-BuOM (M = K, Na, Li)/N 1,N 2-dimethylethane-1,2-diamine (DMEDA) mediated direct C–H arylation of benzene is detailed. The presented mechanistic proposal relies on the complexation and reaction of t-BuOM with DM

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34

Kim, Seoung-Tae, and Mu-Hyun Baik. "Reductive activation of PdII-precatalysts via decarboxylation of pivalate in direct C–H arylation reactions." Chemical Communications 56, no. 89 (2020): 13868–71. http://dx.doi.org/10.1039/d0cc06085b.

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A novel Pd<sup>II</sup> precursor activation by pivalate was discovered. Pivalate was found to decarboxylate and act as a reductant, suggesting an alternative explanation for the superior performance of its use in Pd-catalyzed direct C–H arylation reactions.

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35

Cui, Yuxin, Yanxing Jia, and Zhiyao Lu. "Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions." Synthesis 2011, no. 16 (2011): 2595–99. http://dx.doi.org/10.1055/s-0030-1260603.

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36

Ackermann, Lutz, Andreas Althammer, and Robert Born. "Catalytic Arylation Reactions by CH Bond Activation with Aryl Tosylates." Angewandte Chemie International Edition 45, no. 16 (2006): 2619–22. http://dx.doi.org/10.1002/anie.200504450.

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37

Ngo, Thang Ngoc, Frank Janert, Peter Ehlers, et al. "Pd(0)-catalyzed domino C–N coupling/hydroamination/C–H arylation reactions: efficient synthesis and photophysical properties of azaindolo[1,2-f]phenanthridines." Organic & Biomolecular Chemistry 14, no. 4 (2016): 1293–301. http://dx.doi.org/10.1039/c5ob02274f.

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A series of new 7- and 4-azaindolo[1,2-f]phenanthridines were synthesized by a domino Pd(0)-catalyzed reaction, which involves three sequential steps: C–N coupling, hydroamination, and intramolecular C–H arylation.

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38

Shrivastava, Priyanka, and Swapan Kumar Biswas. "Recent development of Ni-catalyzed C-H activation." Journal of Environmental, Pharmaceutical and Sustainability Science 1, no. 2 (2025): 21–38. https://doi.org/10.52756/jepss.2025.v01.i02.002.

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In recent years, progress in synthetic organic chemistry has been propelled by light-induced reactions, especially by combining photoredox catalysis with nickel catalysis to facilitate cross-coupling reactions that were previously unattainable. Our group embarked on exploring the activation of nickel catalysts through light over the past 5 years, aiming to develop gentle and selective C(sp3)−H cross-coupling reactions by light exposure, eliminating a Ni−Cl bond. Inspired by Nocera laboratory findings, we envisioned using light-induced chlorine atoms to facilitate hydrogen atom transfer (HAT),

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39

Zhao, Lingyu, Guodong Shen, Tongxin Zhang, Zhen Wang та Yuhua Liang. "Pd/C-Catalyzed Intramolecular C–H Arylation for the Synthesis of Phenanthridinones and Dibenzo-α-pyrones". SynOpen 01, № 01 (2017): 0129–37. http://dx.doi.org/10.1055/s-0036-1591503.

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Pd/C was found to be an efficient and convenient metal catalyst for intramolecular C–H arylation reactions in the synthesis of phenanthridinones and dibenzo-α-pyrones. A variety of phenanthridinones and dibenzo-α-pyrones were synthesized under the highly active catalytic system of Pd/C-KOAc-DMA in moderate to excellent yields. The high catalytic activity, high recyclability, low costs, and ease of removal of Pd/C, combined with its commercial availability, render this protocol attractive for both synthetic and industrial applications.

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40

Verrier, Cécile, Pierrik Lassalas, Laure Théveau, et al. "Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series." Beilstein Journal of Organic Chemistry 7 (November 29, 2011): 1584–601. http://dx.doi.org/10.3762/bjoc.7.187.

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Catalytic direct (hetero)arylation of (hetero)arenes is an attractive alternative to traditional Kumada, Stille, Negishi and Suzuki–Miyaura cross-coupling reactions, notably as it avoids the prior preparation and isolation of (hetero)arylmetals. Developments of this methodology in the oxazole series are reviewed in this article. Methodologies, selectivity, mechanism and future aspects are presented.

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41

Chmovzh, Timofey N., Timofey A. Kudryashev, Daria A. Alekhina, and Oleg A. Rakitin. "Palladium-Catalyzed Direct (Het)arylation Reactions of Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole and 4,8-Dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)." Molecules 28, no. 9 (2023): 3977. http://dx.doi.org/10.3390/molecules28093977.

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Palladium-catalyzed direct (het)arylation reactions of strongly electron-withdrawing tricyclic benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative were studied; the conditions for the selective formation of mono- and bis-aryl derivatives were found. The reaction of 4,8-dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) with thiophenes in the presence of palladium acetate as a catalyst and potassium pivalate as a base, depending on the conditions used, selectively gave both mono- and bis-thienylated benzo-bis-thiadiazoles in low to moderate yields; arenes were found to be i

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42

Vu Minh, Cuong, Anh Nguyen Thai, Nam Phan Thanh Son, and Tung Nguyen Thanh. "Copper ferrite catalyst for direct arylation of acidic C-H bonds in azoles with aryl aldehydes." Vietnam Journal of Catalysis and Adsorption 10, no. 4 (2021): 68–72. http://dx.doi.org/10.51316/jca.2021.070.

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Coupling reagents toward direct arylation of C2-H bonds in aryl azoles are often limited to aryl halides. Herein we report a functionalization of the acidic sp2 C-H bonds in benzothiazoles with benzaldehyde derivatives. Reactions proceeded in the presence of commercially ready CuFe2O4 catalyst. Scope of functional groups included chloro, nitro, cyano, and ester groups.

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Wang, Xiaochen, Yuechen Li, Jianfeng Li, Yuan Zhang, Jinjun Shao, and Yongfang Li. "Direct Arylation Synthesis of Small Molecular Acceptors for Organic Solar Cells." Molecules 28, no. 8 (2023): 3515. http://dx.doi.org/10.3390/molecules28083515.

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In recent years, small molecular acceptors (SMAs) have extensively promoted the progress of organic solar cells (OSCs). The facile tuning of chemical structures affords SMAs excellent tunability of their absorption and energy levels, and it gives SMA-based OSCs slight energy loss, enabling OSCs to achieve high power conversion efficiencies (e.g., >18%). However, SMAs always suffer complicated chemical structures requiring multiple-step synthesis and cumbersome purification, which is unfavorable to the large-scale production of SMAs and OSC devices for industrialization. Direct arylation cou

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Rossi, Sergio, Fabian Herbrik, Simonetta Resta, and Alessandra Puglisi. "Supported Eosin Y as a Photocatalyst for C-H Arylation of Furan in Batch and Flow." Molecules 27, no. 16 (2022): 5096. http://dx.doi.org/10.3390/molecules27165096.

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Eosin Y is one of the most popular organic dyes used as a photoredox catalyst and is largely employed in photochemical reactions both as a homogeneous and heterogeneous photocatalyst after immobilization. Immobilization of Eosin Y onto a solid support has many advantages, such as the possibility of recovery and reuse of the photocatalyst and the possibility of its use under flow conditions. In this paper, we report our findings on the immobilization of Eosin Y onto Merrifield resin and its application in the direct photochemical arylation of furan with aryldiazonium salts. The synthesized supp

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Koiso, Satoshi, Kosuke Sato, and Shinsuke Inagi. "Electrochemical C–H Arylation of Polythiophenes By Using Aryldiazonium Salts." ECS Meeting Abstracts MA2024-02, no. 53 (2024): 3626. https://doi.org/10.1149/ma2024-02533626mtgabs.

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Electrochemical post-functionalization is a polymer reaction method in which a nucleophile (or electrophile) attacks the doping state of a π-conjugated polymer generated by applying a potential to the polymer film1,2). This reaction scheme faces various challenges, including the limitation that only conducting polymers can be used as a precursor in the solid state. In order to solve this problem, development of a liquid-phase electrochemical post-functionalization is required. However, it is also known that electron transfer between electrodes and dissolved polymers does not proceed efficientl

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Rocaboy, Ronan, David Dailler, Florian Zellweger, et al. "Domino Pd0 -Catalyzed C(sp3 )-H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates." Angewandte Chemie 130, no. 37 (2018): 12307–11. http://dx.doi.org/10.1002/ange.201807097.

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Rocaboy, Ronan, David Dailler, Florian Zellweger, et al. "Domino Pd0 -Catalyzed C(sp3 )-H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates." Angewandte Chemie International Edition 57, no. 37 (2018): 12131–35. http://dx.doi.org/10.1002/anie.201807097.

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Shahrisa, Aziz, Reza Teimuri-Mofrad, and Mahdi Gholamhosseini-Nazari. "Chemoselective Sequential Reactions for the Synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines." Synlett 26, no. 08 (2015): 1031–38. http://dx.doi.org/10.1055/s-0034-1380323.

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Novel sequential Betti–Ullmann and Betti–C–H activation reactions for the synthesis of 12H-benzo[a]xanthenes and dihydro-1H-naphtho[1,2-e][1,3]oxazines have been developed. Depending on the used conditions selective Ullmann-type arylation or α-C-H aryloxylation of 2-bromophenyl alkylaminonaphthols occurred. A simple, fast, green, and high-yielding method for the synthesis of aminonaphthols catalyzed by bismuth(III) chloride under solvent-free conditions is reported.

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Liu, Yunyun, Yi Zhang, Xiaoji Cao та Jie-Ping Wan. "Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp3)–H arylation". Beilstein Journal of Organic Chemistry 12 (3 червня 2016): 1122–26. http://dx.doi.org/10.3762/bjoc.12.108.

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The synthesis of β-arylated alkylamides via alkyl C–H bond arylation has been realized by means of direct one-pot reactions of acyl chlorides, aryl iodides and 8-aminoquinoline. Depending on the structure of the starting materials, both single and double β-arylated alkylamides could be accessed.

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Oschmann, Michael, Linus Johansson Holm, Monireh Pourghasemi-Lati, and Oscar Verho. "Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry." Molecules 25, no. 2 (2020): 361. http://dx.doi.org/10.3390/molecules25020361.

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Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, tw

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