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Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules.

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.

SUBMITTER: Gibson SM

PROVIDER: S-EPMC6099344 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules.

Gibson Samantha M SM D'Oyley Jarryl M JM Higham Joe I JI Sanders Kate K Laserna Victor V Aliev Abil E AE Sheppard Tom D TD

European journal of organic chemistry 20180718 29

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 rin ...[more]

PMID: 30147439

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