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

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Author: Grafiati

Published: 6 September 2023

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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 (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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2

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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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 (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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5

Dhankhar, Jyoti, and Ilija Čorić. "Direct C–H Arylation." CHIMIA 76, no. 9 (September 21, 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. Additionally, the common presence of a number of C–H bonds in a molecule raises the issue of site-selectivity because differentiation of C–H bonds that are in sterically and electronically similar environments is a challenge. We discuss selected recent developments that are a part of the long-term research interest in mild and selective C–H activation reactions with a focus on the replacement of C–H bonds with C–aryl groups and an emphasis on the work of our group.

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6

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 sequential chemoselective C–O arylation and C–H arylation. The 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3.

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7

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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8

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (May 14, 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 aryloxepines are also discussed.1 Introduction2 Benzyl Reagents with Leaving Groups3 Quinone Methide Mediated Reactions4 Arylation of Benzyl Halides5 C–H Activation of Methylene6 Reactions of Carbonyl Compounds7 Conclusions

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9

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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10

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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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 (July 6, 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 this review, we mainly focus on the recent advance in direct redox-neutral radical C–H functionalization of heteroarenes. Herein, the direct C–H arylation, C–H alkylation, and C–H fluoroalkylation of heteroarenes are represented respectively, providing practical routes to C–C bond formation.1 Introduction2 C–H Arylation of Heteroarenes with Aryl Radicals3 C–H Alkylation of Heteroarenes with Alkyl Radicals4 C–H Fluoroalkylation of Heteroarenes with Fluorine-Containing Carbon Radicals5 Concluding Remarks

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12

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (June 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 and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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13

Kónya, Krisztina, and Zoltán Sipos. "Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C–H Activation." Synthesis 50, no. 08 (March 7, 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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14

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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15

Wang, Shoufeng, Shuya Xing, Yingying Zhang, Yafei Fan, Huaiqing Zhao, Jianfeng Wang, Shuxiang Zhang, and Wengui Wang. "The Ag-promoted α-C–H arylation of alcohols." RSC Advances 9, no. 71 (2019): 41847–50. http://dx.doi.org/10.1039/c9ra09954a.

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16

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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17

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 (May 18, 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 dyes. All prepared sensitizers display broad absorption from 350 nm up to 800 nm with high molar extinction coefficients. The dye-sensitized solar cells based on these dyes exhibit a power conversion efficiency in the range of 2.9 to 3.4%.

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18

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 (January 2015): no. http://dx.doi.org/10.1002/chin.201504198.

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19

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 (January 1, 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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20

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 (November 14, 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 calculations have been performed to rationalize the lack of C–H bond reactivity in the ruthenium-catalyzed reaction.

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21

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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22

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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23

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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24

Shchegolkov, Evgeny V., Yanina V. Burgart, Daria A. Matsneva, Sophia S. Borisevich, Renata A. Kadyrova, Iana R. Orshanskaya, Vladimir V. Zarubaev, and Victor I. Saloutin. "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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25

Zhou, Chun-Ni, Zi-Ang Zheng, George Chang, Yuan-Chao Xiao, Yang-Huan Shen, Gen Li, Yu-Min Zhang, Wang-Ming Peng, Liang Wang, and Biao Xiao. "Phosphorus-Containing Groups Assisted Transition Metal Catalyzed C-H Activation Reactions." Current Organic Chemistry 23, no. 2 (April 23, 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 mechanistic study and synthetic applications. The discussion is directed towards C-H olefination, C-H activation/cyclization, C-H arylation, C-H amination, C-H hydroxylation and acetoxylation as well as miscellaneous C-H activation.

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26

Yang, Zhenzhen, Zhenghui Liu, Hongye Zhang, Bo Yu, Yanfei Zhao, Huan Wang, Guipeng Ji, Yu Chen, Xinwei Liu, and Zhimin Liu. "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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27

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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28

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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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(sp²)–H bond arylation reactions.

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30

Cui, Yuxin, Yanxing Jia, and Zhiyao Lu. "Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions." Synthesis 2011, no. 16 (May 26, 2011): 2595–99. http://dx.doi.org/10.1055/s-0030-1260603.

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31

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 (April 10, 2006): 2619–22. http://dx.doi.org/10.1002/anie.200504450.

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32

Kündig, E. Peter, Yixia Jia, Dmitry Katayev, and Masafumi Nakanishi. "Asymmetric Pd-NHC*-catalyzed coupling reactions." Pure and Applied Chemistry 84, no. 8 (July 1, 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. Remarkably, this occurs at high temperature (140–160 °C) via excellent asymmetric recognition of an enantiotopic C–H bond in an unactivated methylene unit.

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33

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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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^II 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

Ngo, Thang Ngoc, Frank Janert, Peter Ehlers, Do Huy Hoang, Tuan Thanh Dang, Alexander Villinger, Stefan Lochbrunner, and Peter Langer. "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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36

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 (June 22, 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 DMEDA (additive), which leads to the formation of different complexes such as SED(M+)…PhI. These complexes mainly involve coordination of the metal ion (from t-BuOM) to the additive and iodobenzene via stabilizing cation–lone pair and cation–π interactions. Such complexation of a metal ion to an additive and iodobenzene not only ensures facile electron transfer to iodobenzene but also provides a lowest energy pathway for the subsequent radical addition and deprotonation step.

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37

Shen, Rui, Wei Zhu, Xiaodong Yan, Tao Li, Yong Liu, Yunxing Li, Siyuan Dai, and Zhi-Guo Gu. "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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38

Zhao, Lingyu, Guodong Shen, Tongxin Zhang, Zhen Wang, and Yuhua Liang. "Pd/C-Catalyzed Intramolecular C–H Arylation for the Synthesis of Phenanthridinones and Dibenzo-α-pyrones." SynOpen 01, no. 01 (March 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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39

Verrier, Cécile, Pierrik Lassalas, Laure Théveau, Guy Quéguiner, François Trécourt, Francis Marsais, and Christophe Hoarau. "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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Rocaboy, Ronan, David Dailler, Florian Zellweger, Markus Neuburger, Christophe Salomé, Eric Clot, and Olivier Baudoin. "Domino Pd0 -Catalyzed C(sp3 )-H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates." Angewandte Chemie 130, no. 37 (August 20, 2018): 12307–11. http://dx.doi.org/10.1002/ange.201807097.

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41

Rocaboy, Ronan, David Dailler, Florian Zellweger, Markus Neuburger, Christophe Salomé, Eric Clot, and Olivier Baudoin. "Domino Pd0 -Catalyzed C(sp3 )-H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates." Angewandte Chemie International Edition 57, no. 37 (August 20, 2018): 12131–35. http://dx.doi.org/10.1002/anie.201807097.

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42

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 (August 10, 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 supported photocatalyst was used in batch reactions under heterogeneous conditions with different aryl diazonium salts, and its recovery and recycle were demonstrated for up to three times. The immobilized photocatalyst was then loaded in a packed-bed reactor and used under continuous flow conditions. The flow reaction allowed the arylated products to be obtained with higher productivity and space-time-yield than the batch in a very short reaction time.

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43

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 (August 20, 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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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 (May 8, 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 inactive in these reactions. It was discovered that direct C–H arylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with bromo(iodo)arenes and -thiophenes in the presence of Pd(OAc)2 and di-tert-butyl(methyl)phosphonium tetrafluoroborate salt is a powerful tool for the selective formation of 4-mono- and 4,8-di(het)arylated benzo-bis-thiadiazoles. Oxidative double C–H hetarylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with thiophenes in the presence of Pd(OAc)2 and silver (I) oxide in DMSO was successfully employed to prepare bis-thienylbenzo-bis-thiadiazoles in moderate yields.

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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 (April 16, 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 coupling reaction via aromatic C-H bonds activation allows for the synthesis of SMAs under mild conditions, and it simultaneously reduces synthetic steps, synthetic difficulty, and toxic by-products. This review provides an overview of the progress of SMA synthesis through direct arylation and summarizes the typical reaction conditions to highlight the field’s challenges. Significantly, the impacts of direct arylation conditions on reaction activity and reaction yield of the different reactants’ structures are discussed and highlighted. This review gives a comprehensive view of preparing SMAs by direct arylation reactions to cause attention to the facile and low-cost synthesis of photovoltaic materials for OSCs.

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46

Tanji, Yutaka, Naoya Mitsutake, Tetsuaki Fujihara, and Yasushi Tsuji. "Steric Effect of Carboxylate Ligands on Pd-Catalyzed Intramolecular C(sp2 )-H and C(sp3 )-H Arylation Reactions." Angewandte Chemie 130, no. 32 (June 19, 2018): 10471–74. http://dx.doi.org/10.1002/ange.201804566.

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47

Tanji, Yutaka, Naoya Mitsutake, Tetsuaki Fujihara, and Yasushi Tsuji. "Steric Effect of Carboxylate Ligands on Pd-Catalyzed Intramolecular C(sp2 )-H and C(sp3 )-H Arylation Reactions." Angewandte Chemie International Edition 57, no. 32 (June 19, 2018): 10314–17. http://dx.doi.org/10.1002/anie.201804566.

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48

Mori, Atsunori, Shigeru Matsuda, Masabumi Takahashi, and Daiki Monguchi. "C-H and C-Si Functionalization of Furan Derivatives: Palladium-Catalyzed Homocoupling and Arylation Reactions." Synlett 2009, no. 12 (July 2009): 1941–44. http://dx.doi.org/10.1055/s-0029-1217537.

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49

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 (March 12, 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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50

Lu, Zhiyao, Yuxin Cui, and Yanxing Jia. "ChemInform Abstract: Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions." ChemInform 42, no. 52 (December 1, 2011): no. http://dx.doi.org/10.1002/chin.201152144.

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