Chem p. 1963 - 1974 (2021)
Update date:2022-08-05
Topics:
Fu, Yue
Liu, Fang-Jie
Liu, Peng
Tang, Jian-Tao
Toste, F. Dean
Wu, Ting-Feng
Ye, Baihua
Zhang, Yue-Jiao
Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.
View MoreShifang Taifeng New Flame Retardant Co., Ltd
Contact:02884721008
Address:tingjiang industrial park, hefeng town
Winchem Industrial Co. Ltd.(expird)
Contact:86-574-83851061 86-574-87083208
Address:Room 905, No.3 Building,East Business Center, 456 Xingning Road, Ningbo City,China
Angelisun(Chongqing) Pharmaceutical Co., LTD.
Contact:+86-23-68030926-816
Address:D1-7 Tech & Entrepreneurs Park, Kecheng Road, Erlang Hi-Tech Areas, Chongqing, China
Contact:732.938.2777
Address:5012 Industrial Road Farmingdale, NJ 07727
Contact:+86-25-83719363
Address:106-7 Chunnan Rd, Chunxi Town, Gaochun, Nanjing, China
Doi:10.1016/S0040-4039(00)01674-9
(2000)Doi:10.1002/1521-3765(20001103)6:21<3958::AID-CHEM3958>3.0.CO;2-Y
(2000)Doi:10.1016/S0020-1693(00)81935-0
(1976)Doi:10.1021/jo005541l
(2000)Doi:10.1002/1521-3773(20001002)39:19<3473::AID-ANIE3473>3.0.CO;2-E
(2000)Doi:10.1021/ol0068344
(2000)