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Micelle-Enabled Photoassisted Selective Oxyhalogenation of Alkynes in Water under Mild Conditions

Lucie Finck, Jeremy Brals, Bhavana Pavuluri, Fabrice Gallou and Sachin Handa*

*Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292, United States, Email: sachin.handalouisville.edu

L. Finck, J. Brals, B. Pavuluri, F. Gallou, S. Handa, J. Org. Chem., 2018, 83, 7366-7372.

DOI: 10.1021/acs.joc.7b03143 (free Supporting Information)


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Abstract

Selective oxyhalogenations of alkynes were achieved in water under very mild conditions in the presence of inexpensive halogenating reagents, such as N-bromosuccinimide and N-chlorosuccinimde, and FI-750-M as amphiphile. No halogenation at the aromatic rings was detected. Reaction medium and catalyst can be recycled.

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Key Words

α-Bromoketones, α-Chloroketones, NBS, NCS, Green Chemistry, Photochemistry


ID: J42-Y2018