Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules

被引：7

作者：

Gibson, Samantha M. ^{[1
]}

D'Oyley, Jarryl M. ^{[1
]}

Higham, Joe I. ^{[1
]}

Sanders, Kate ^{[1
]}

Laserna, Victor ^{[1
]}

Aliev, Abil E. ^{[1
]}

Sheppard, Tom D. ^{[1
]}

机构：

[1] UCL, Christopher Ingold Labs, 20 Gordon St, London WC1H 0AJ, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 29期

基金：

英国工程与自然科学研究理事会;

关键词：

Halogenation; Alkynes; Alcohols; Heterocycles; Ketones; BETA-HYDROXY KETONES; POT 3-COMPONENT SYNTHESIS; DIELS-ALDER REACTIONS; PROPARGYLIC ALCOHOLS; EFFICIENT METHOD; REDUCTION; GOLD; 3-HALOFURANS; 3-CHLOROFURANS; SUBSTITUENT;

D O I：

10.1002/ejoc.201800668

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：4018 / 4028

页数：11

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