Synthesis of δ-Bromo
γ,δ-Unsaturated
Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates
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Abstract
Palladium-catalyzed regio- and stereoselective intermolecular
tandem
reaction of electron-deficient alkynes, CuBr<sub>2</sub>, and allylic
alcohol to synthesize δ-bromo-γ,δ-unsaturated carbonyls
was developed. A mechanism involving bromopalladation of alkyne, followed
by insertion of allylic alcohol and allylic hydrogen shift, is proposed.
The shift of allylic hydrogen is the rate-limiting step in this reaction