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Journal articles on the topic 'Arylation coupling'

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Author: Grafiati

Published: 25 May 2024

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1

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

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

2

Barde, E., A. Guérinot, and J. Cossy. "α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions." Synthesis 51, no. 01 (December 7, 2018): 178–84. http://dx.doi.org/10.1055/s-0037-1611358.

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Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Cross-Coupling2.1 Palladium Catalysis2.2 Nickel Catalysis3 Kumada–Corriu Cross-Coupling3.1 Nickel Catalysis3.2 Iron Catalysis3.3 Cobalt Catalysis4 Negishi Cross-Coupling5 Hiyama Cross-Coupling6 Conclusion

3

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

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

4

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

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

5

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%.

6

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.

7

El Abbouchi, Abdelmoula, Jamal Koubachi, Nabil El Brahmi, and Said El Kazzouli. "Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation." Mediterranean Journal of Chemistry 9, no. 5 (November 27, 2019): 347–54. http://dx.doi.org/10.13171/mjc1911271124sek.

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A short and practical arylation of imidazo[1,2-a]pyridine and imidazole derivatives with aryl halides or aryl boronic acids as coupling partners was successfully carried out using phosphine-free (SIPr)Pd(allyl)Cl as the catalyst [SIPr: (N,N’-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)] ((SIPr)Pd(allyl)Cl complex). 3,6-disubstituted imidazo[1,2-a]pyridine and 5-substituted imidazole compounds were obtained in good to excellent yields in only 1h under microwave-assisted C-H arylation and Suzuki-Miyaura coupling reaction conditions.

8

Zhu, Hui, Xing Liu, Cai-Zhu Chang, and Zhi-Bing Dong. "Copper-Catalyzed C–S Cross-Coupling Reaction: S-Arylation of Arylthioureas." Synthesis 49, no. 23 (August 22, 2017): 5211–16. http://dx.doi.org/10.1055/s-0036-1590879.

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A simple and efficient copper-catalyzed S-arylation of arylthioureas was developed. Arylthioureas were smoothly converted into aryl-isothioureas with good yield by copper-catalyzed S-arylation. The features of this method include the use of a ligand-free catalyst, good yield, short reaction time, and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.

9

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

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

10

Cao, Zhi-Chao, Da-Gang Yu, Ru-Yi Zhu, Jiang-Bo Wei, and Zhang-Jie Shi. "Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis." Chemical Communications 51, no. 13 (2015): 2683–86. http://dx.doi.org/10.1039/c4cc10084k.

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A direct arylation to furnish diarylmethanes from benzyl alcohols was realized through Pd(PPh₃)₄-catalyzed Suzuki–Miyaura coupling via benzylic C–O activation in the absence of any additives. The arylation is compatible with various functional groups. This development provides an atom- and step-economic way to approach a diarylmethane scaffold under mild and environmentally benign conditions.

11

Raina, Gaurav, Prakash Kannaboina, Nagaraju Mupparapu, Sushil Raina, Qazi Naveed Ahmed, and Parthasarathi Das. "Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2134–47. http://dx.doi.org/10.1039/c9ob00144a.

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12

Marquise, Nada, Vincent Dorcet, Floris Chevallier, and Florence Mongin. "Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes." Org. Biomol. Chem. 12, no. 41 (2014): 8138–41. http://dx.doi.org/10.1039/c4ob01629g.

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13

Wang, Xiaochen, Kai Wang, and Mingfeng Wang. "Synthesis of conjugated polymers via an exclusive direct-arylation coupling reaction: a facile and straightforward way to synthesize thiophene-flanked benzothiadiazole derivatives and their copolymers." Polymer Chemistry 6, no. 10 (2015): 1846–55. http://dx.doi.org/10.1039/c4py01627k.

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14

Jin, Rongwei, Charles Beromeo Bheeter, and Henri Doucet. "Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes." Beilstein Journal of Organic Chemistry 10 (May 27, 2014): 1239–45. http://dx.doi.org/10.3762/bjoc.10.123.

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The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases the desired 5-arylation products in moderate to good yields using only 0.5 mol % of a phosphine-free and air-stable palladium catalyst. Then, from these 5-arylthiophenes, a second palladium-catalysed C–H bond functionalization at C2 of the thiophene ring allows the synthesis of 2,5-diarylthiophenes with two different aryl units.

15

Faradhiyani, Alanna, Qiao Zhang, Keisuke Maruyama, Junpei Kuwabara, Takeshi Yasuda, and Takaki Kanbara. "Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling." Materials Chemistry Frontiers 2, no. 7 (2018): 1306–9. http://dx.doi.org/10.1039/c7qm00584a.

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16

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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17

Pacheco-Benichou, Alexandra, Thierry Besson, and Corinne Fruit. "Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes." Catalysts 10, no. 5 (April 28, 2020): 483. http://dx.doi.org/10.3390/catal10050483.

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Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners.

18

Mu, Yucheng, Xiaodong Tan, Yemin Zhang, Xiaobi Jing, and Zhuangzhi Shi. "Pd(ii)-catalyzed β-C–H arylation of O-methyl ketoximes with iodoarenes." Organic Chemistry Frontiers 3, no. 3 (2016): 380–84. http://dx.doi.org/10.1039/c5qo00438a.

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19

Mahindra, Amit, and Rahul Jain. "Regiocontrolled palladium-catalyzed and copper-mediated C–H bond functionalization of protectedl-histidine." Org. Biomol. Chem. 12, no. 23 (2014): 3792–96. http://dx.doi.org/10.1039/c4ob00430b.

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20

Chen, Chunxiang, Daniel Hernández Maldonado, Damien Le Borgne, Fabienne Alary, Barbara Lonetti, Benoît Heinrich, Bertrand Donnio, and Kathleen I. Moineau-Chane Ching. "Synthesis of benzothiadiazole-based molecules via direct arylation: an eco-friendly way of obtaining small semi-conducting organic molecules." New Journal of Chemistry 40, no. 9 (2016): 7326–37. http://dx.doi.org/10.1039/c6nj00847j.

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21

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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22

Zhang, Lei, and Xile Hu. "Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds." Chemical Science 11, no. 39 (2020): 10786–91. http://dx.doi.org/10.1039/d0sc01445a.

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23

Zu, Weisai, Shuai Liu, Xin Jia, and Liang Xu. "Chemoselective N-arylation of aminobenzene sulfonamides via copper catalysed Chan–Evans–Lam reactions." Organic Chemistry Frontiers 6, no. 9 (2019): 1356–60. http://dx.doi.org/10.1039/c8qo01313f.

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24

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.

25

Mendis, Shehani N., and Jon A. Tunge. "Decarboxylative dearomatization and mono-α-arylation of ketones." Chemical Communications 52, no. 49 (2016): 7695–98. http://dx.doi.org/10.1039/c6cc03672d.

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26

Washington, Jack B., Michele Assante, Chunhui Yan, David McKinney, Vanessa Juba, Andrew G. Leach, Sharon E. Baillie, and Marc Reid. "Trialkylammonium salt degradation: implications for methylation and cross-coupling." Chemical Science 12, no. 20 (2021): 6949–63. http://dx.doi.org/10.1039/d1sc00757b.

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The dual reactivity of N,N,N-trimethylanilinium salts towards arylation and methylation is decoupled in this mechanistic investigation to enable more strategic application of these salts in either reaction class.

27

Smari, Imen, Liqin Zhao, Kedong Yuan, Hamed Ben Ammar, and Henri Doucet. "Reactivity of bromofluorenes in palladium-catalysed direct arylation of heteroaromatics." Catal. Sci. Technol. 4, no. 10 (2014): 3723–32. http://dx.doi.org/10.1039/c4cy00771a.

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28

Nageswar Rao, D., Sk Rasheed, Ram A. Vishwakarma, and Parthasarathi Das. "Copper-catalyzed sequential N-arylation of C-amino-NH-azoles." Chem. Commun. 50, no. 85 (2014): 12911–14. http://dx.doi.org/10.1039/c4cc05628k.

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29

Paul, Sanjay, Hari Datta Khanal, Chayan Dhar Clinton, Sung Hong Kim, and Yong Rok Lee. "Pd(TFA)2-catalyzed direct arylation of quinoxalinones with arenes." Organic Chemistry Frontiers 6, no. 2 (2019): 231–35. http://dx.doi.org/10.1039/c8qo01250d.

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30

Liu, Shuai, Weisai Zu, Jinli Zhang, and Liang Xu. "Chemoselective N-arylation of aminobenzamides via copper catalysed Chan–Evans–Lam reactions." Organic & Biomolecular Chemistry 15, no. 44 (2017): 9288–92. http://dx.doi.org/10.1039/c7ob02491f.

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31

Correa, Arkaitz, Béla Fiser, and Enrique Gómez-Bengoa. "Iron-catalyzed direct α-arylation of ethers with azoles." Chemical Communications 51, no. 69 (2015): 13365–68. http://dx.doi.org/10.1039/c5cc05005g.

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32

Siva Reddy, A., K. Ranjith Reddy, D. Nageswar Rao, Chaitanya K. Jaladanki, Prasad V. Bharatam, Patrick Y. S. Lam, and Parthasarathi Das. "Copper(ii)-catalyzed Chan–Lam cross-coupling: chemoselective N-arylation of aminophenols." Organic & Biomolecular Chemistry 15, no. 4 (2017): 801–6. http://dx.doi.org/10.1039/c6ob02444k.

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33

Chen, Yuanguang, Fangyu Du, Fengyang Chen, Qifan Zhou, and Guoliang Chen. "Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation." Synthesis 51, no. 24 (October 14, 2019): 4590–600. http://dx.doi.org/10.1055/s-0039-1690702.

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In the selective N-arylation of amines or azoles with aryl halides, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

34

Seifert, Sabine, David Schmidt, and Frank Würthner. "A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides." Organic Chemistry Frontiers 3, no. 11 (2016): 1435–42. http://dx.doi.org/10.1039/c6qo00421k.

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35

Sharma, Alpesh K., Hemant Joshi, Renu Bhaskar, Satyendra Kumar, and Ajai K. Singh. "Palladacycles of sulfated and selenated Schiff bases of ferrocene-carboxaldehyde as catalysts for O-arylation and Suzuki–Miyaura coupling." Dalton Transactions 46, no. 8 (2017): 2485–96. http://dx.doi.org/10.1039/c7dt00083a.

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36

Shu, Bing, Xiao-Tong Wang, Zi-Xuan Shen, Tong Che, Mei Zhong, Jia-Lin Song, Hua-Jie Kang, Hui Xie, Luyong Zhang, and Shang-Shi Zhang. "Iridium-catalyzed arylation of sulfoxonium ylides and arylboronic acids: a straightforward preparation of α-aryl ketones." Organic Chemistry Frontiers 7, no. 14 (2020): 1802–8. http://dx.doi.org/10.1039/d0qo00543f.

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37

Wagner, Patrick, Maud Bollenbach, Christelle Doebelin, Frédéric Bihel, Jean-Jacques Bourguignon, Christophe Salomé, and Martine Schmitt. "t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water." Green Chem. 16, no. 9 (2014): 4170–78. http://dx.doi.org/10.1039/c4gc00853g.

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38

Puthiaraj, Pillaiyar, and Wha-Seung Ahn. "Synthesis of copper nanoparticles supported on a microporous covalent triazine polymer: an efficient and reusable catalyst for O-arylation reaction." Catalysis Science & Technology 6, no. 6 (2016): 1701–9. http://dx.doi.org/10.1039/c5cy01590a.

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39

Cong, Zhanqing, Feng Gao, and Hong Liu. "Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C–H bonds utilizing amino acids as a directing group." RSC Advances 9, no. 19 (2019): 10820–24. http://dx.doi.org/10.1039/c9ra00749k.

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40

Lutz, J. Patrick, Stephen T. Chau, and Abigail G. Doyle. "Nickel-catalyzed enantioselective arylation of pyridine." Chemical Science 7, no. 7 (2016): 4105–9. http://dx.doi.org/10.1039/c6sc00702c.

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41

Basu, Souradeep, Alexander H. Sandtorv, and David R. Stuart. "Imide arylation with aryl(TMP)iodonium tosylates." Beilstein Journal of Organic Chemistry 14 (May 11, 2018): 1034–38. http://dx.doi.org/10.3762/bjoc.14.90.

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Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.

42

Chen, Xin, Yunyun Bian, Baichuan Mo, Peng Sun, Chunxia Chen, and Jinsong Peng. "Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions." RSC Advances 10, no. 42 (2020): 24830–39. http://dx.doi.org/10.1039/d0ra04592f.

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43

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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44

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.

45

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.

46

Morimoto, Koji, Yusuke Ohnishi, Daichi Koseki, Akira Nakamura, Toshifumi Dohi, and Yasuyuki Kita. "Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling." Organic & Biomolecular Chemistry 14, no. 38 (2016): 8947–51. http://dx.doi.org/10.1039/c6ob01764a.

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Abstract:

We have developed a direct oxidative C–H bond arylation of pyrroles with various aromatic compounds via stabilized pyrrolyl iodonium(iii) salts generated from modified hypervalent iodine(iii) and TMSCl as an activator.

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Kumar, K. Anil, Prakash Kannaboina, D. Nageswar Rao, and Parthasarathi Das. "Nickel-catalyzed Chan–Lam cross-coupling: chemoselective N-arylation of 2-aminobenzimidazoles." Organic & Biomolecular Chemistry 14, no. 38 (2016): 8989–97. http://dx.doi.org/10.1039/c6ob01307d.

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Nasrollahzadeh, Mahmoud. "Advances in Magnetic Nanoparticles-Supported Palladium Complexes for Coupling Reactions." Molecules 23, no. 10 (October 4, 2018): 2532. http://dx.doi.org/10.3390/molecules23102532.

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Abstract:

Carbon‒carbon (C‒C) and carbon‒heteroatom (C‒X) bonds that form via transition-metal-catalyzed processes have been extensively used in the organic synthesis and preparation of natural products and important compounds such as heterocycles, biologically active molecules, and dendrimers. Among the most significant catalysts, magnetic nanoparticles-supported palladium complexes are very effective, versatile, and heterogeneous catalysts for a wide range of C‒C and C‒X coupling reactions due to their reusability, thermal stability, and excellent catalytic performance. In this review, recent advances to develop magnetic nanoparticles supported palladium complexes, including their preparation, characterization, catalytic application, and reusability in the formation of both C‒C and C‒X bonds, by authors such as Sonogashira, Heck, Suzuki‒Miyaura, and Stille, and a few examples concerning N-arylation, S-arylation, and Csp2-P coupling reactions are discussed.

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Sasmal, Arpan, Thierry Roisnel, Jitendra K. Bera, Henri Doucet, and Jean-François Soulé. "Reactivity of 3-Bromofuran in Pd-Catalyzed C–H Bond Arylation toward the Synthesis of 2,3,5-Triarylfurans." Synthesis 51, no. 17 (May 7, 2019): 3241–49. http://dx.doi.org/10.1055/s-0037-1611819.

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Arylation of the C–H bond at the C2 position of 3-bromofuran is achieved using aryl bromides as coupling partners in the presence of phosphine-free Pd(OAc)2/KOAc in DMA. This procedure gives C2,C5-di- and even C2,C4,C5-triarylated 3-bromofuran derivatives when larger amounts of aryl bromides are employed. In addition, C2,C3,C5-triarylated furans—containing three different aryl groups—are synthesized via a C2–H bond arylation/Suzuki reaction/C5–H bond arylation sequence.

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Gao, Hui, Xinyu Chen, Pei-Long Wang, Meng-Meng Shi, Ling-Long Shang, Heng-Yi Guo, Hongji Li, and Pinhua Li. "Electrochemical benzylic C–H arylation of xanthenes and thioxanthenes without a catalyst and oxidant." Organic Chemistry Frontiers 9, no. 7 (2022): 1911–16. http://dx.doi.org/10.1039/d1qo01925b.

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