Organocatalysis as a safe practical method for the stereospecific dibromination of unsaturated compounds.

Gloria Hernández-Torres, Bin Tan, Carlos F Barbas

Index: Org. Lett. 14(7) , 1858-61, (2012)

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Abstract

Organocatalytic stereospecific dibromination of a wide variety of functionalized alkenes was achieved using a stable, inexpensive halogen source, 1,3-dibromo 5,5-dimethylhydantoin, and a simple thiourea catalyst at room temperature. The presence of a tertiary amine enhanced the rate of the dibromination reaction, and yields were good in various solvents, including aqueous solvents. The procedure was extended to alkynes and aromatic rings and to dichlorination reactions by using the 1,3-dichloro hydantoin derivative.