Issue 46, 2017

Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides

Abstract

Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.

Graphical abstract: Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides

Supplementary files

Article information

Article type
Paper
Submitted
26 Sep 2017
Accepted
07 Nov 2017
First published
13 Nov 2017

Org. Biomol. Chem., 2017,15, 9830-9836

Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides

J. Hamel, T. Hayashi, M. Cloutier, P. R. Savoie, O. Thibeault, M. Beaudoin and J. Paquin, Org. Biomol. Chem., 2017, 15, 9830 DOI: 10.1039/C7OB02406A

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