Open AccessGeneral Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
Author(s) -
Lei Guo,
Mingbin Yuan,
Yanyan Zhang,
Fang Wang,
Shuaishuai Zhu,
Osvaldo Gutiérrez,
Lingling Chu
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.0c08823
Subject(s) - chemistry , enantioselective synthesis , nickel , photoredox catalysis , aryl , alkyl , catalysis , combinatorial chemistry , visible spectrum , photochemistry , organic chemistry , photocatalysis , physics , optoelectronics
A visible-light-promoted photoredox/nickel protocol for the enantioselective three-component carboarylation of alkenes with tertiary and secondary alkyltrifluoroborates and aryl bromides is described. This redox-neutral protocol allows for facile and divergent access to a wide array of enantioenriched β-alkyl-α-arylated carbonyls, phosphonates, and sulfones in high yields and excellent enantioselectivities from readily available starting materials. We also report a modular and enantioselective synthesis of flurbiprofen analogs and piragliatin lead compound to demonstrate synthetic utility. Experimental and computational mechanistic studies were performed to gain insights into the mechanism and origin of chemo- and enantioselectivity.