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

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

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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2

Maiti, Debabrata, Sumon Basak, and Jyoti Prasad Biswas. "Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents." Synthesis 53, no. 18 (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 regio

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3

Wencel-Delord, Joanna, and Françoise Colobert. "Challenging Atroposelective C–H Arylation." SynOpen 04, no. 04 (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 f

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4

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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5

Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé та 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 (28 жовтня 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

Patra, Tuhin, Sudip Nandi, Santosh K. Sahoo, and Debabrata Maiti. "Copper mediated decarboxylative direct C–H arylation of heteroarenes with benzoic acids." Chemical Communications 52, no. 7 (2016): 1432–35. http://dx.doi.org/10.1039/c5cc08367b.

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Copper mediated decarboxylative direct C–H arylation of 5-membered heteroarenes with aryl carboxylic acids is developed using the molecular oxygen as sole oxidant. Copper plays the dual role in decarboxylation and C–H arylation.

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7

Lamblin, Marc, François-Xavier Felpin, Guillaume Naturale, and Jean Dessolin. "Direct C-H Arylation of Quinones with Anilines." Synlett 23, no. 11 (2012): 1621–24. http://dx.doi.org/10.1055/s-0031-1291163.

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8

Ihanainen, Netta E., Esa T. T. Kumpulainen, and Ari M. P. Koskinen. "Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes." European Journal of Organic Chemistry 2015, no. 15 (2015): 3226–29. http://dx.doi.org/10.1002/ejoc.201500288.

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9

To, Ching Tat, Wu Yang, and Kin Shing Chan. "Porphyrins and Phthalocyanines Catalyzed Direct CH Arylation." Chinese Journal of Chemistry 34, no. 10 (2016): 955–61. http://dx.doi.org/10.1002/cjoc.201600442.

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10

Sharma, Upendra, Atanu Modak, Soham Maity, Arun Maji, and Debabrata Maiti. "ChemInform Abstract: Direct Arylation via C-H Activation." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518322.

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11

Gigant, Nicolas, and Jan-E. Bäckvall. "Aerobic Direct C–H Arylation of Nonbiased Olefins." Organic Letters 16, no. 17 (2014): 4432–35. http://dx.doi.org/10.1021/ol501924t.

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12

Perry, Ian B., Thomas F. Brewer, Patrick J. Sarver, Danielle M. Schultz, Daniel A. DiRocco, and David W. C. MacMillan. "Direct arylation of strong aliphatic C–H bonds." Nature 560, no. 7716 (2018): 70–75. http://dx.doi.org/10.1038/s41586-018-0366-x.

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13

Kan, Jian, Shijun Huang, Huaiqing Zhao, Jin Lin, and Weiping Su. "Photoinduced C-H direct arylation of unactivated arenes." Science China Chemistry 58, no. 8 (2015): 1329–33. http://dx.doi.org/10.1007/s11426-015-5377-y.

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14

Wei, Xiao-Hong, Gang-Wei Wang, and Shang-Dong Yang. "Enantioselective synthesis of arylglycine derivatives by direct C–H oxidative cross-coupling." Chemical Communications 51, no. 5 (2015): 832–35. http://dx.doi.org/10.1039/c4cc07361d.

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A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C–H arylation of N-aryl glycine esters with aryl boric acids by direct C–H oxidative cross-coupling has been performed. This work successfully integrates the direct C–H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.

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15

Li, Xiang-Chun, Yibo Xue, Wan Song та ін. "Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based π-Conjugated Molecules for Optoelectronics". Research 2020 (30 серпня 2020): 1–12. http://dx.doi.org/10.34133/2020/9075697.

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Controllable direct C-H arylation with high regioselectivity is highly desirable yet remains a formidable challenge. Herein, a facile regioselective direct C-H arylation is developed for efficient construction of a variety of symmetrical dithienophthalimide-based π-conjugated molecules. The resulting methodology is applicable to a wide range of substrates, from electron-rich units to electron-deficient units with large steric end groups. Aryl halides have been confirmed to be able to couple with dithienophthalimide (DTI) via direct C-H arylation, showing high regioselectivity. Varying the func

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16

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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17

Font, Marc, Andrew R. A. Spencer, and Igor Larrosa. "meta-C–H arylation of fluoroarenes via traceless directing group relay strategy." Chemical Science 9, no. 35 (2018): 7133–37. http://dx.doi.org/10.1039/c8sc02417k.

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The first example of direct meta-C–H arylation of fluoroarenes to provide valuable meta-fluorobiaryls is achieved by exploiting CO<sub>2</sub> as a transient directing group that enables complete regiochemical control of the arylation event.

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18

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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19

Qiao, Huijie, Suyan Sun, Fan Yang, et al. "Palladium-catalyzed direct C–H arylation of ferrocenecarboxamides with aryl halides." RSC Advances 6, no. 64 (2016): 59319–26. http://dx.doi.org/10.1039/c6ra11972g.

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20

Čerňa, Igor, Radek Pohl, and Michal Hocek. "The first direct C–H arylation of purine nucleosides." Chemical Communications, no. 45 (2007): 4729. http://dx.doi.org/10.1039/b714253f.

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21

Li, Bijin, Brianna Lawrence, Guigen Li та Haibo Ge. "Ligand‐Controlled Direct γ‐C−H Arylation of Aldehydes". Angewandte Chemie International Edition 59, № 8 (2020): 3078–82. http://dx.doi.org/10.1002/anie.201913126.

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22

Li, Bijin, Brianna Lawrence, Guigen Li та Haibo Ge. "Ligand‐Controlled Direct γ‐C−H Arylation of Aldehydes". Angewandte Chemie 132, № 8 (2020): 3102–6. http://dx.doi.org/10.1002/ange.201913126.

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23

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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24

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 synthesi

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25

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 (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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26

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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27

Lane, Benjamin S., and Dalibor Sames. "Direct C−H Bond Arylation: Selective Palladium-Catalyzed C2-Arylation ofN-Substituted Indoles." Organic Letters 6, no. 17 (2004): 2897–900. http://dx.doi.org/10.1021/ol0490072.

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28

Frippiat, Steven, Christine Baudequin, Christophe Hoarau, et al. "Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles." Synlett 31, no. 10 (2020): 1015–21. http://dx.doi.org/10.1055/s-0040-1708003.

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The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.

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29

Mohr, Yorck, Gaëlle Hisler, Léonie Grousset, et al. "Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes." Green Chemistry 22, no. 10 (2020): 3155–61. http://dx.doi.org/10.1039/d0gc00917b.

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30

Djakovitch, Laurent, and François-Xavier Felpin. "Direct C sp2H and C sp3H Arylation Enabled by Heterogeneous Palladium Catalysts." ChemCatChem 6, no. 8 (2014): 2175–87. http://dx.doi.org/10.1002/cctc.201402288.

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31

Zhu, Tonghao, Shimin Xie, Pornchai Rojsitthisak та Jie Wu. "Recent advances in the direct β-C(sp2)–H functionalization of enamides". Organic & Biomolecular Chemistry 18, № 8 (2020): 1504–21. http://dx.doi.org/10.1039/c9ob02649e.

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Recent advances in the direct β-C(sp<sup>2</sup>)–H functionalization of enamides, mainly including arylation, alkenylation, alkynylation, alkylation, acylation, sulfonylation, phosphorylation, and others, are reported.

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32

Yang, Woo-Ram, Yong-Sung Choi, and Jin-Hyun Jeong. "Efficient synthesis of polymethoxyselenoflavones via regioselective direct C–H arylation of selenochromones." Organic & Biomolecular Chemistry 15, no. 14 (2017): 3074–83. http://dx.doi.org/10.1039/c7ob00118e.

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A simple direct C–H arylation of two difficult coupling partners, selenochromones and electron-rich aryl bromide, has been developed, affording diverse polymethoxyselenoflavones with great efficiency and high selectivity.

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33

Moazzam, Ali, and Farnaz Jafarpour. "Chlorophyll-catalyzed photochemical regioselective coumarin C–H arylation with diazonium salts." New Journal of Chemistry 44, no. 39 (2020): 16692–96. http://dx.doi.org/10.1039/d0nj02012e.

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34

You, Liyan, Jiazhi He, and Jianguo Mei. "Tunable green electrochromic polymers via direct arylation polymerization." Polymer Chemistry 9, no. 43 (2018): 5262–67. http://dx.doi.org/10.1039/c8py01105b.

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35

Gong, Hao, Yiwen Yang, Zechao Wang, and Chunxiang Kuang. "An easy direct arylation of 5-pyrazolones." Beilstein Journal of Organic Chemistry 9 (October 8, 2013): 2033–39. http://dx.doi.org/10.3762/bjoc.9.240.

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A mild, efficient and catalytic ligand-free method for the direct arylation of 5-pyrazolones by Pd-catalyzed C–H bond activation is reported. The process smoothly proceeds and yields are moderate to excellent.

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36

Song, Juan, Yali Li, Wei Sun, et al. "Efficient palladium-catalyzed C(sp2)–H activation towards the synthesis of fluorenes." New Journal of Chemistry 40, no. 11 (2016): 9030–33. http://dx.doi.org/10.1039/c6nj02033j.

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37

Muselli, Mickaël, Christine Baudequin, Christophe Hoarau, and Laurent Bischoff. "Pd-Catalyzed direct C–H functionalization of imidazolones with aryl- and alkenyl halides." Chemical Communications 51, no. 4 (2015): 745–48. http://dx.doi.org/10.1039/c4cc07917e.

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38

Tamang, Sem Raj, та James D. Hoefelmeyer. "Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)". Beilstein Journal of Organic Chemistry 12 (15 грудня 2016): 2757–62. http://dx.doi.org/10.3762/bjoc.12.272.

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We report direct arylation of arylhalides with unactivated sp2 C–H bonds in benzene and naphthalene using a copper(I) catalyst featuring an ambiphilic ligand, (quinolin-8-yl)dimesitylborane. Direct arylation could be achieved with 0.2 mol % catalyst and 3 equivalents of base (KO(t-Bu)) at 80 °C to afford TON ≈160–190 over 40 hours.

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39

Yu, Peng, Guangyou Zhang, Fan Chen, and Jiang Cheng. "Direct arylation of benzoxazole C–H bonds with iodobenzene diacetates." Tetrahedron Letters 53, no. 34 (2012): 4588–90. http://dx.doi.org/10.1016/j.tetlet.2012.06.076.

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40

Zhang, Yuan, Jack Chang Hung Lee, Matthew R. Reese, Brian P. Boscoe, John M. Humphrey, and Christopher J. Helal. "5-Aryltetrazoles from Direct C–H Arylation with Aryl Bromides." Journal of Organic Chemistry 85, no. 8 (2020): 5718–23. http://dx.doi.org/10.1021/acs.joc.0c00085.

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41

Jiang, Hui, Ana Bellomo, Mengnan Zhang, et al. "Palladium-Catalyzed Direct C–H Arylation of 3-(Methylsulfinyl)thiophenes." Organic Letters 20, no. 9 (2018): 2522–25. http://dx.doi.org/10.1021/acs.orglett.8b00599.

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42

Yang, Fan, Yangjie Wu, Zhiwu Zhu, Junli Zhang, and Yanan Li. "Direct ortho-arylation of 2-arylbenzoxazoles via C–H activation." Tetrahedron 64, no. 28 (2008): 6782–87. http://dx.doi.org/10.1016/j.tet.2008.04.099.

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43

Norinder, Jakob, Arimasa Matsumoto, Naohiko Yoshikai, and Eiichi Nakamura. "Iron-Catalyzed Direct Arylation through Directed C−H Bond Activation." Journal of the American Chemical Society 130, no. 18 (2008): 5858–59. http://dx.doi.org/10.1021/ja800818b.

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44

Gowrisankar, Saravanan, and Jayasree Seayad. "AgONO-Assisted Direct CH Arylation of Heteroarenes with Anilines." Chemistry - A European Journal 20, no. 40 (2014): 12754–58. http://dx.doi.org/10.1002/chem.201403640.

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45

Gigant, Nicolas, and Jan-E. Baeckval. "ChemInform Abstract: Aerobic Direct C-H Arylation of Nonbiased Olefins." ChemInform 46, no. 9 (2015): no. http://dx.doi.org/10.1002/chin.201509073.

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46

Ihanainen, Netta E., Esa T. T. Kumpulainen, and Ari M. P. Koskinen. "ChemInform Abstract: Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes." ChemInform 46, no. 37 (2015): no. http://dx.doi.org/10.1002/chin.201537105.

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47

Lamblin, Marc, Guillaume Naturale, Jean Dessolin, and Francois-Xavier Felpin. "ChemInform Abstract: Direct C-H Arylation of Quinones with Anilines." ChemInform 43, no. 40 (2012): no. http://dx.doi.org/10.1002/chin.201240087.

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48

Liu, De-Peng, Qi Chen, Yan-Chao Zhao, Li-Min Zhang, Ai-Di Qi, and Bao-Hang Han. "Fluorinated Porous Organic Polymers via Direct C–H Arylation Polycondensation." ACS Macro Letters 2, no. 6 (2013): 522–26. http://dx.doi.org/10.1021/mz4001699.

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49

Jiang, Huanfeng, Wanfei Yang, Huoji Chen, Jianxiao Li, and Wanqing Wu. "Palladium-catalyzed aerobic oxidative allylic C–H arylation of alkenes with polyfluorobenzenes." Chem. Commun. 50, no. 54 (2014): 7202–4. http://dx.doi.org/10.1039/c4cc02023e.

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50

Gao, Pan, Li Liu, Zhuangzhi Shi, and Yu Yuan. "Iridium(iii)-catalyzed regioselective direct arylation of sp2 C–H bonds with diaryliodonium salts." Organic & Biomolecular Chemistry 14, no. 29 (2016): 7109–13. http://dx.doi.org/10.1039/c6ob01145d.

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