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Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Non-Catalyzed Reactions

D'Oyley, JM; Aliev, AE; Sheppard, TD; (2014) Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Non-Catalyzed Reactions. Angewandte Chemie International Edition , 53 (40) pp. 10747-10750. 10.1002/anie.201405348. Green open access

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Abstract

The regioselective conversion of propargylic alcohols into previously unreported α,α-diiodo-β-hydroxyketones was achieved by treatment with N-iodosuccinimide in the presence of a gold catalyst. The corresponding α,α-dichloro-β-hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transformations can be used to prepare potentially useful halogenated building blocks. Preliminary mechanistic studies suggest that the reaction involves participation of the acetonitrile solvent in the formation of a 5-halo-1,3-oxazine intermediate.

Type: Article
Title: Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Non-Catalyzed Reactions
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/anie.201405348
Publisher version: http://dx.doi.org/10.1002/anie.201405348
Language: English
Additional information: © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Keywords: gold, halogenation, homogeneous catalysis, ketones, reaction mechanisms
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1443430
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