期刊
ACS CATALYSIS
卷 10, 期 15, 页码 8168-8176出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01462
关键词
Suzuki cross-coupling; sulfoxide; C-S bond activation; NHC-Pd; DFT
资金
- National Natural Science Foundation of China [NSFC 21571087, 21673156]
- Major Projects of Natural Science Research in Jiangsu Province [15KJA150004]
The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the Suzuki-Miyaura reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reactions showed good functional group compatibility, proceeded well under mild conditions, and provided biaryls in yields of up to 96%. A wide range of useful functional groups, such as fluoro, chloro, ether, hydroxyl, amide, cyano, keto, trimethylsilyl (TMS), and ester were tolerated under the reaction conditions; however, the use of phenylboronic anhydride and arylboronic acid pinacol esters generally would lead low yields. Good regioselectivity for the electron-poor phenyl group was achieved when unsymmetrical diphenyl sulfoxides were used. The protocol is applicable at the gram scale even with half the amount of catalyst. Density functional theory calculations were performed to investigate the reaction mechanism, indicating that the reaction occurred through oxidative addition, transmetalation, and reductive elimination to provide the final coupling product.
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