Bromination of olefins with HBr and DMSO

The Journal of Organic Chemistry
Megha Karki, Jakob Magolan

Abstract

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

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Citations

May 21, 2016·Chemical Reviews·Indranirekha SaikiaProdeep Phukan
Apr 21, 2017·Journal of the American Chemical Society·Nobuya SakaiHenry J Snaith
Dec 3, 2015·Angewandte Chemie·Alexander J CresswellScott E Denmark
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ligeng WangJun Hu
Nov 24, 2018·European Journal of Organic Chemistry·Rene EbuleBo Xu
May 20, 2015·The Journal of Organic Chemistry·Kanchan MalIndrajit Das
Nov 28, 2018·Journal of the American Chemical Society·Gao-Feng ZhaHua-Li Qin
Sep 18, 2020·The Journal of Organic Chemistry·Amar Ramchandra MohiteOfer Reany
Nov 26, 2021·Chemical Communications : Chem Comm·Xianheng SongYong Zou
Dec 9, 2021·Chemistry : a European Journal·Jorge PascualAntonio Abate

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