Enantioselective Pd-catalyzed dearomative reductive Heck and domino Heck-Suzuki reactions of 2-CF3-indoles
Ren-Xiao Liang1, Jian-Fei Chen1, Ying-Ying Huang1
1College of Chemical Engineering, State Key Laboratory Breeding Base of Green Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou, 310014, China. liangrx@zjut.edu.cn.
Abstract:
Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck-Suzuki reaction of 2-CF3-indoles have been developed. Using Pd(OAc)2/(R)-Synphos as the catalyst and Et3SiH as a hydride source, a variety of indolines bearing a 2-trifluoromethyl quaternary stereocenter were obtained via a dearomative reductive Heck reaction. Alternatively, using Pd(dba)2/phosphoramidite as the catalyst and Ar4BNa as a coupling partner, structurally diverse indolines containing two vicinal carbon stereocenters were afforded through the domino dearomative Heck-Suzuki reaction.
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