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

Journal of the American Chemical Society
Lei GuoLingling Chu

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.

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Citations

Aug 13, 2021·Accounts of Chemical Research·Laura M Wickham, Ramesh Giri
Sep 1, 2021·Journal of the American Chemical Society·Luchuan JuTianning Diao
Sep 21, 2021·Journal of the American Chemical Society·Sii Hong LauAbigail G Doyle
Oct 7, 2021·Chemical Reviews·Liang ChangZhiwei Zuo
Oct 29, 2021·Organic & Biomolecular Chemistry·Wu ZhangHaohua Huo
Sep 30, 2021·Angewandte Chemie·Yuan-Yuan ChengLi-Zhu Wu
Nov 19, 2021·Chemical Reviews·Amy Y ChanDavid W C MacMillan

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