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Letters in Organic Chemistry

Author(s): Lívia T.C. Crespo, Mônica R. Senra, Pierre M. Esteves* and Marcio C.S. de Mattos*

DOI: 10.2174/1570178615666180803152951

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Tribromoisocyanuric Acid as a Green Cohalogenating Reagent: An Efficient Transformation of Alkynes into α,α-Dibromoketones and Vicinal Dibromoalkenes

Page: [627 - 632] Pages: 6

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Abstract

The co-halogenation reaction of alkynes with tri-bromoisocyanuric acid in acetic acid, followed by aqueous work-up produced α,α-di-bromoketones (44-84%), while the reaction in aqueous acetonitrile in the presence of KBr produced vicinal di-bromoalkenes (66-86%). The usefulness of the methodology was demonstrated employing green metrics for the comparison of TBCA with analogous N-halo reagents in co-halogenation reactions of alkynes.

Keywords: Bromination, electrophilic addition, halogenation, regioselectivity, green chemistry, alkenes, alkynes, ketones.