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Updated: Mar 3, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Lewis acid/NHC dual catalysis for regioselective vicinal decarboxylative carbonylation-acylation of alkenes
Mao-Lin Yang1, Xiao-Feng Wu1,2
1Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a 18059 Rostock Germany xiao-feng.wu@catalysis.de.
Abstract:
Vicinal difunctionalization of alkenes offers a powerful route to complex carbon architectures by installing two distinct groups. Herein, we describe a novel Lewis acid-thiazolium NHC catalytic system that enables precise control of a single-electron-transfer (SET) process to achieve CO-incorporated vicinal decarboxylative carbonylation-acylation of alkenes. The reaction is proposed to proceed via a concerted SET between the enolate form of the Breslow intermediate and a Lewis acid-activated NHPI ester, followed by CO trapping and regioselective recombination of multiple radical intermediates to install two distinct carbonyl groups. This strategy constitutes a new platform for C1 exchange and enables efficient CO incorporation even with sterically demanding or conformationally rigid alkyl radicals.
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