Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules

Overview

Journal European J Org Chem

Specialty Biochemistry

Date 2018 Aug 28

PMID 30147439

Authors

Samantha M Gibson

Jarryl M DOyley

Joe I Higham

Kate Sanders

Victor Laserna

Abil E Aliev

Tom D Sheppard

Affiliations

Soon will be listed here.

Abstract

In this paper we outline how dihalohydration reactions of propargylic alcohols can be used to access a wide variety of useful halogenated building blocks. A novel procedure for dibromohydration of alkynes has been developed, and a selection of dichloro and dibromo diols and cyclic ethers were synthesized. The dihalohydration of homo-propargylic alcohols provides a useful route to 3-halofurans, which were shown to readily undergo cycloaddition reactions under mild conditions. Finally, a novel ring expansion of propargylic alcohols containing a cyclopropylalkyne provides access to halogenated alkenylcyclobutanes.

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