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

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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

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Publication details

The article was received on 20 Jan 2019, accepted on 20 Mar 2019 and first published on 29 Mar 2019


Article type: Communication
DOI: 10.1039/C9OB00151D
Citation: Org. Biomol. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB00151D

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