Electrochemical Gold‐Catalyzed 1,2‐Difunctionalization of C−C Multiple Bonds

Herein, we disclose the first report of 1,2‐difunctionalization of C−C multiple bonds using electrochemical gold redox catalysis. By adopting the electrochemical strategy, the inherent π‐activation and cross‐coupling reactivity of gold catalysis are harnessed to develop the oxy‐alkynylation of allen...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-09, Vol.62 (37), p.e202308636-n/a
Main Authors: Kumar, Anil, Shukla, Khyati, Ahsan, Salman, Paul, Amit, Patil, Nitin T.
Format: Article
Language:English
Subjects:
Allene Functionalization
Catalysis
Cross coupling
Electrochemistry
Gold
Gold Catalysis
NMR
Nuclear magnetic resonance
Oxidants
Oxidizing agents
Oxy-Alkynylation
Reaction mechanisms
Redox Catalysis
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Summary:Herein, we disclose the first report of 1,2‐difunctionalization of C−C multiple bonds using electrochemical gold redox catalysis. By adopting the electrochemical strategy, the inherent π‐activation and cross‐coupling reactivity of gold catalysis are harnessed to develop the oxy‐alkynylation of allenoates under external‐oxidant‐free conditions. Detailed mechanistic investigations such as 31P NMR, control experiments, mass studies, and cyclic voltammetric (CV) analysis have been performed to support the proposed reaction mechanism. The first report on electrochemical AuI/AuIII catalysis for 1,2‐difunctionalization of C−C multiple bonds has been presented. This external‐oxidant‐free approach utilizes the anodic oxidation of vinyl‐AuI to vinyl‐AuIII complexes to achieve oxy‐alkynylation of allenoates to access alkyne‐substituted butenolides in an undivided cell.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202308636