Bromination of Olefins with HBr and DMSO

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.

Chlorothiomethylation of Alkynes with HCl and Dimethyl Sulfoxide: An Efficient Approach to (E)‐α‐chloro‐β‐(methylthio)alkenes

“…[2] As is well known, direct addition of heteroatom-heteroatom bonds or two separate heteroatoms to the carbon-carbon triple bond of alkynes in one pot provides a straightforward, effective, mild, and flexible synthesis of 1,2-diheteroatom-substituted alkene derivatives. [3] To date, many successful additions have been developed to access 1,2-dihalo-alkenes, [4] 1,2-bisthiolated alkenes, [5] 1,2-bisalkoxyl-alkenes, [6] and alkenes cross-substituted with two heteroatom groups. [7] In recent years, chlorosulfonation [8] addition reactions have attracted particular interest and emerged as a flourishing research area, because the corresponding adducts are versatile substrates in organic transformations, and can be converted into diverse alkenyl sulfides, sulfones, chlorides, and many other polyfunctionalized compounds [9] by further transformations of the chloro and sulfone moieties.…”

Origin of Sn(ii) oxidation in tin halide perovskites

“…The oxidation of many different types of organic compounds in DMSO in the presence of hydrogen halides has been widely studied. [18][19][20][21] Through the in situ generation of halodimethylsulfonium halides 19 it is possible to carry out oxidative halogenations on olefins 20 or aromatic compounds, 21 among others. In this sense, any I 2 generated would also be able to oxidise SnI 2 to SnI 4 .…”

Metal‐Free, Facile Synthesis of Sulfenylated Chromones and Indoles Promoted by an Aqueous HBr−DMSO System

“…Hence the need of an in‐situ preparative method for their generation followed by their use in organic synthesis. In this context, various oxidants have been investigated for the oxidation of halide ion such as O 2 H 2 O 2 – Oxone– Selectfluor DMSO– and metal‐based oxidants. [1 ° ,p] Nevertheless, continuous investigations for the development of greener/safer reaction conditions in this field are essential since the available protocols suffer from selectivity issue, waste generation, expensive reagents and longer reaction time .…”