Issue 18, 2019

Au-Catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement between allylic alcohols and chloroalkynes

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.

Graphical abstract: Au-Catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement between allylic alcohols and chloroalkynes

Supplementary files

Article information

Article type
Communication
Submitted
20 Jan 2019
Accepted
20 Mar 2019
First published
29 Mar 2019

Org. Biomol. Chem., 2019,17, 4435-4439

Au-Catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement between allylic alcohols and chloroalkynes

C. Liu, J. Xu, L. Ding, H. Zhang, Y. Xue and F. Yang, Org. Biomol. Chem., 2019, 17, 4435 DOI: 10.1039/C9OB00151D

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