Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P­(V) species (i.e., fluorophosphorane) and a silyl enol...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-11, Vol.143 (44), p.18394-18399
Main Authors: Fujimoto, Hayato, Kusano, Momoka, Kodama, Takuya, Tobisu, Mamoru
Format: Article
Language:English
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Summary:We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P­(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C–C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P­(III)/P­(V) manifold.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c10042