A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane–dimethyl sulfide

Dibromoborane–dimethyl sulfide (BHBr2–SMe2) displays high degrees of chemo- and regioselectivity during the brominative cleavage of the epoxy group into vicinal bromohydrins in the presence of alkene, alkyne, allene, ether, acetal and acetonide, besides its hydroborating ability. Several reducible functional groups, such as chloride, aldehyde, ketone, azide, ester, nitrile and tert-amino ester, have been successfully accommodated during the epoxide opening process.

Graphical abstractRegio- and chemoselective cleavage of epoxides into β-bromohydrins utilizing the commercially available reagent, BHBr2–SMe2, is described. Several reactive and reducible functional groups, such as, alkene, alkyne, allene, ethers, acetal, ketal, chloride, aldehyde, ketone, azide, ester, nitrile and tert-amino ester, have been successfully accommodated during the epoxide opening reactions.Figure optionsDownload full-size imageDownload as PowerPoint slide