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General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2020-11-19 , DOI: 10.1021/jacs.0c08823
Lei Guo 1 , Mingbin Yuan 2 , Yanyan Zhang 1 , Fang Wang 1 , Shengqing Zhu 1 , Osvaldo Gutierrez 2 , Lingling Chu 1
Affiliation  

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.

中文翻译:

可见光双光氧化还原/镍催化对映选择性三组分碳芳基化烯烃的通用方法

描述了一种可见光促进的光氧化还原/镍协议,用于烯烃与叔和仲烷基三氟硼酸盐和芳基溴化物的对映选择性三组分碳化。这种氧化还原中性协议允许从容易获得的起始材料中以高产率和出色的对映选择性轻松和不同地访问各种富含对映体的 β-烷基-α-芳基化羰基、膦酸盐和砜。我们还报告了氟比洛芬类似物和吡格列汀先导化合物的模块化和对映选择性合成,以证明合成效用。进行了实验和计算机制研究,以深入了解化学和对映选择性的机制和起源。
更新日期:2020-11-19
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