Au-Catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement between allylic alcohols and chloroalkynes
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Updated: Jan 26, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Congrong Liu1, Jin Xu, Lianghui Ding
1School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu 211167, China. congrong@njit.edu.cn.
Abstract:
An efficient protocol for the synthesis of γ,δ-unsaturated α-chloroketones has been developed via Au-catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement. In the presence of 1 mol% JohnPhosAuCl and 1 mol% NaBArF, a broad range of allylic alcohols smoothly underwent the tandem intermolecular hydroalkoxylation/Claisen rearrangement with aromatic, vinylic or aliphatic chloroalkynes to give structurally diverse γ,δ-unsaturated α-chloroketones in excellent yields. Importantly, high Z/E selectivity was achieved. Other advantages are widespread availability of the substrates, compatibility with a broad range of functional groups and mild reaction conditions.
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