Synlett
DOI: 10.1055/a-1374-9384
cluster
Modern Nickel-Catalyzed Reactions

Visible-Light-Mediated Z-Stereoselective Monoalkylation of β,β-Dichlorostyrenes by Photoredox/Nickel Dual Catalysis

Mehdi Abdellaoui
,
Alexandre Millanvois
,
Etienne Levernier
,
,
The authors thank the Agence Nationale de la Recherche (Grant No. ANR-17-CE07-0018, HyperSilight (PhD grant to EL)), the Centre National de la Recherche Scientifique (CNRS), and Sorbonne Université for financial support.


Abstract

Metal-catalyzed alkylation of 1,1-dihalovinyl moiety commonly suffers from both a lack of stereoselectivity and the overreaction leading to the dialkylation product. The methodology described herein features a new pathway to alkylate stereoselectively β,β-dichlorostyryl substrates to provide the Z-trisubstituted olefin only with fair to good yields. This cross-coupling reaction bears on the smooth and photoinduced formation of a C-centered radical that engages in a nickel-catalyzed organometallic cycle to form the key Csp2–Csp3 bond.

Supporting Information



Publication History

Received: 18 December 2020

Accepted after revision: 26 January 2021

Publication Date:
27 January 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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