- Rhodium-catalyzed decarbonylation cross-coupling reactions of aromatic aldehydes and arylboronic acids via C–C bond activation directed by a guide group chelation
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A rhodium-catalyzed decarbonylative cross-coupling reaction of benzoquinoline-10-carbaldehydes with arylboronic acids through chelation-assisted sp2 C–CHO bond activation has been developed. A variety of functional groups substituted phenylboronic acids or benzoquinoline-10-carbaldehydes are compatible with the reaction under the optimized reaction conditions, the corresponding 10-phenylbenzo[h]quinoline derivatives were obtained in moderate to good yields. The method affords a useful strategy for the synthesis of N-heterocyclic biaryl compounds via rhodium-catalyzed sp2 C–CHO bond activation.
- Geng, Shudong,Liu, Guanchen,Yu, Xiaobo
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- Expeditious and Solvent-Free Nickel-Catalyzed C?H Arylation of Arenes and Indoles
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An efficient solvent-free nickel-catalyzed method for C?H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono-arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel-catalyzed C?H arylation by monochelate assistance and symbolizes a rare precedent in solvent-free C?H arylation. Mechanistic investigations by various controlled reactions, kinetic studies, and deuterium labeling experiments suggest that the arylation follows a single electron transfer (SET) pathway involving the turnover-limiting C?H nickelation process.
- Jagtap, Rahul A.,Soni, Vineeta,Punji, Benudhar
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p. 2242 - 2248
(2017/05/29)
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- Site-selective C-H/C-N activation by cooperative catalysis: Primary amides as arylating reagents in directed C-H arylation
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Direct C-H arylation of nonacidic C(sp)-H bonds with primary amides as arylating reagents via highly chemoselective C-H/C-N/C-C cleavages has been accomplished for the first time. The key to the success is the cooperative combination of rhodium(I) catalys
- Meng, Guangrong,Szostak, Michal
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p. 7251 - 7256
(2017/11/09)
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- Efficient Approach to Construct Unsymmetrical Biaryls through Oxidative Coupling Reactions of Aromatic Primary Alcohols and Arylboronic Acids with a Rhodium Catalyst
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Unsymmetrical biaryls were synthesized by oxidative coupling reactions between aromatic primary alcohols and arylboronic acids through the C-C bond cleavage of the primary alcohols chelated with a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap, environmentally friendly, and easily accessible substrates.
- Yu, Xiaobo,Wang, Jingjing,Guo, Weijie,Tian, Yun,Wang, Jianhui
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supporting information
p. 1876 - 1884
(2016/07/06)
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- Cobalt-catalyzed C-H bond functionalizations with aryl and alkyl chlorides
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Inexpensive cobalt catalysts derived from N-heterocylic carbenes (NHC) allowed efficient catalytic C-H bond arylations on heteroaryl-substituted arenes with widely available aryl chlorides, which set the stage for the preparation of sterically hindered tr
- Punji, Benudhar,Song, Weifeng,Shevchenko, Grigory A.,Ackermann, Lutz
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supporting information
p. 10605 - 10610
(2013/08/23)
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- Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
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2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,
- Ilies, Laurean,Kobayashi, Motoaki,Matsumoto, Arimasa,Yoshikai, Naohiko,Nakamura, Eiichi
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supporting information; experimental part
p. 593 - 596
(2012/04/23)
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- Rhodium-catalyzed cross-coupling reactions of carboxylate and organoboron compounds via chelation-assisted C-C bond activation
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A new rhodium-catalyzed decarbonylated coupling reaction of ethyl benzo[h]quinoline-10-carboxylate and organoboron compounds that occurs through chelation-assisted sp2 C-COOEt bond activation was described. In this system CuCl played a very important role, and a five-membered rhodacycle was also involved as a key intermediate. Various functionalities were compatible in the reaction, and the desired products were obtained in good to excellent yields. DFT calculations on the mechanisms of this reaction using a Rh(I) model catalyst have also been carried out.
- Wang, Jingjing,Liu, Bowen,Zhao, Haitao,Wang, Jianhui
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p. 8598 - 8607
(2013/02/23)
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- Direct cross-coupling of C-H bonds with grignard reagents through cobalt catalysis
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Go go Grignard! The first highly regioselective, cobalt-catalyzed C-H transformation of benzo[h]quinoline and phenylpyridine derivatives with Grignard reagents at room temperature has been achieved (see scheme). Both aryl and alkyl Grignard reagents showed significant reactivity.
- Li, Bin,Wu, Zhen-Hua,Gu, Yi-Fan,Sun, Chang-Liang,Wang, Bai-Quan,Shi, Zhang-Jie
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supporting information; experimental part
p. 1109 - 1113
(2011/04/22)
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- RuCi3 xH2O-catalyzed direct arylation of arenes with aryl chlorides in the presence of triphenylphosphine
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A study was conducted to demonstrate the RuCl3·xH 2O catalytic system for direct arylation of arenes with aryl chlorides. The phenylation of benzo[h]quinoline with chlorobenzene was investigated under preliminary studies. The reaction of benzo[h]quinoline and chlorobenzene N-methyl-2-pyrrolidone (NMP) formed Ph as the only product in 86-93% yields at 120-130 8C in the presence of K2CO3 using 5 mol% RuCl3·xH2O and 10 mol% PPh3. It was observed that the presence of an excess of ligand did not affect formation of Ph, while sub-stoichiometric ligand amounts led to a reduced conversion for benzo[h]quinoline. The arylation and benzylation of benzo[h]quinoline with various aryl chlorides was also investigated under the study.
- Luo, Ning,Yu, Zhengkun
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supporting information; experimental part
p. 787 - 791
(2010/05/19)
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- Efficient Rh(I)-Catalyzed direct arylation and alkenylation of arene C-H bonds via decarbonylation of benzoic and cinnamic anhydrides
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Efficient rhodium(I)-catalyzed regioselective direct arylation and alkenylation of aromatic C-H bonds has been realized with aromatic carboxylic and cinnamic anhydrides as the coupling partners via decarbonylation and C-H activation under phosphine-free c
- Jin, Weiwei,Yu, Zhengkun,He, Wei,Ye, Wenjing,Xiao, Wen-Jing
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supporting information; experimental part
p. 1317 - 1320
(2009/10/02)
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