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Organocatalysis as a Safe Practical Method for the Stereospecific Dibromination of Unsaturated Compounds

Gloria Hernández-Torres, Bin Tan and Carlos F. Barbas III*

*The Skaggs Institute for Chemical Biology and Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 Torrey Pines Road, La Jolla, California 92037, United States, Email:

G. Hernández-Torres, B. Tan, C. F. Barbas III, Org. Lett., 2012, 14, 1858-1861.

DOI: 10.1021/ol300456x (free Supporting Information)

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Organocatalytic stereospecific dibromination of various functionalized alkenes was achieved using a simple thiourea catalyst and 1,3-dibromo 5,5-dimethylhydantoin as a stable, inexpensive halogen source at room temperature. The procedure was extended to alkynes and aromatic rings and to dichlorination reactions by using the 1,3-dichloro hydantoin derivative.

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Key Words

dibromination, organocatalysis, 1,3-dibromo 5,5-dimethylhydantoin

ID: J54-Y2012-1050