Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules

作者:Gibson Samantha M; D'Oyley Jarryl M; Higham Joe I; Sanders Kate; Laserna Victor; Aliev Abil E; Sheppard Tom D*
来源:European Journal of Organic Chemistry, 2018, 2018(29): 4018-4028.
DOI:10.1002/ejoc.201800668

摘要

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.

  • 出版日期2018-8-7