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可见光氧化还原/镍双催化对映选择性三组分烯烃芳基化反应的通用方法
作者:小柯机器人 发布时间:2020/11/21 21:03:07

以东华大学储玲玲课题组为首的国际团队在对映选择性三组分烯烃芳基化反应(three-component carboarylation of alkenes)方面取得新进展。相关论文于2020年11月19日发表于国际顶尖学术期刊《美国化学会志》上。

该研究描述了一种可见光促进的、由光氧化还原和镍双催化的、发生在烯烃与叔烷基/仲烷基三氟硼酸盐和芳基溴化物之间的对映选择性三组分芳基化反应。该氧化还原中性的合成方法可以利用容易获得的起始原料,以高收率和优异的对映选择性轻松而多样地获得大量手性富集的β-烷基-α-芳基化羰基化合物、膦酸酯和砜。

研究人员还报道了氟比洛芬类似物和piragliatin先导化合物的模块化和对映选择性合成,以证明该合成方法的实用性。此外,团队还通过实验与计算化学研究,揭示了该反应的机理以及其化学和手性选择性的来源。

附:英文原文

Title: General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis

Author: Lei Guo, Mingbin Yuan, Yanyan Zhang, Fang Wang, Shengqing Zhu, Osvaldo Gutierrez, Lingling Chu

Issue&Volume: November 19, 2020

Abstract: 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.

DOI: 10.1021/jacs.0c08823

Source: https://pubs.acs.org/doi/10.1021/jacs.0c08823

 

期刊信息

JACS:《美国化学会志》,创刊于1879年。隶属于美国化学会,最新IF:14.612
官方网址:https://pubs.acs.org/journal/jacsat
投稿链接:https://acsparagonplus.acs.org/psweb/loginForm?code=1000