Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source

Lei Wang; Lele Zhai; Jinyan Chen; Yulin Gong; Peng Wang; Huilin Li; Xuegong She

doi:10.1021/acs.joc.1c02906

Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source

J Org Chem. 2022 Mar 4;87(5):3177-3183. doi: 10.1021/acs.joc.1c02906. Epub 2022 Feb 8.

Authors

Lei Wang¹, Lele Zhai¹, Jinyan Chen¹, Yulin Gong¹, Peng Wang¹, Huilin Li¹, Xuegong She¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, Gansu, P. R. China.

PMID: 35133816
DOI: 10.1021/acs.joc.1c02906

Abstract

A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction proceeds under mild reaction conditions without the use of a catalyst and an external oxidant. Various sorts of alkene substrates are transformed into the corresponding 1,2-dibrominated products in good to excellent yields with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.