Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-catalyzed and Noncatalyzed Reactions

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2014 Aug 23

PMID 25147077

Citations 5

Authors

Jarryl M DOyley

Abil E Aliev

Tom D Sheppard

Affiliations

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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.

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