Premium
Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
Author(s) -
Gibson Samantha M.,
D'Oyley Jarryl M.,
Higham Joe I.,
Sanders Kate,
Laserna Victor,
Aliev Abil E.,
Sheppard Tom D.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800668
Subject(s) - chemistry , cycloaddition , combinatorial chemistry , ring (chemistry) , organic chemistry , molecule , halogenation , catalysis
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.