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Synlett 2021; 32(15): 1513-1518
DOI: 10.1055/a-1374-9384
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
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.
Key words
cross-coupling - stereoselective alkylation - radical - dichlorostyrenes - bis(catecholato)silicates - dual catalysis - counterion - nickelSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1374-9384.
- Supporting Information
Publication History
Received: 18 December 2020
Accepted after revision: 26 January 2021
Accepted Manuscript online:
27 January 2021
Article published online:
15 February 2021
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