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Synthesis 2018; 50(21): 4325-4335
DOI: 10.1055/s-0037-1609560
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide

Rui Ding
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Jiaqi Li
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Wenyi Jiao
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Mengru Han
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Yongguo Liu
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Hongyu Tian*
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Baoguo Sun*
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing, 100048, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
› Author AffiliationsFinancial support from the National Key Research and Development Program (2016YFD0400801), the Beijing Postdoctoral Research Foundation (2017-22-011) and the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions (CIT&TCD20140306) is gratefully acknowledged.
Further Information

Publication History

Received: 28 April 2018

Accepted after revision: 21 June 2018

Publication Date:
08 August 2018 (online)

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Abstract

The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.

Key words

bromination - dimethyl sulfoxide - oxalyl bromide - alkenes - alkynes - ketones - bromodimethylsulfonium salt

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609560.
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