Synthesis and derivatization of ethynyl alpha,alpha-dibromomethyl ketones: formation of highly functionalized vinyl triflates.
[reaction: see text] We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.
Rankin
Trent
T
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Tykwinski
Rik R
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