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A Photoirradiative Phase-Vanishing Method: Efficient Generation of HBr from Alkanes and Molecular Bromine and Its Use for Subsequent Radical Addition to Terminal Alkenes

Hiroshi Matsubara*, Masaaki Tsukida, Daisuke Ishihara, Kenji Kuniyoshi, Ilhyong Ryu*

*Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan, Email:,

H. Matsubara, M. Tsukida, D. Ishihara, K. Kuniyoshi, I. Ryu, Synlett, 2010, 2014-2018.

DOI: 10.1055/s-0030-1258482


In a triphasic phase-vanishing system comprised of an alkane, perfluorohexanes, and bromine, photoirradiation efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields.

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Key Words

fluorous solvent, phase-vanishing, photoirradiation, bromination, hydrogen bromide

ID: J60-Y2010-2170