Abstract

2-Bromoallyl acetate has been shown to be an efficient substrate for Ni(II)/Cr(II)-mediated coupling reactions with a variety of aliphatic and aryl aldehydes. Surprisingly, elimination of acetate from the intermediate vinylchromium species does not appear to compete with carbon−carbon bond formation. In addition, the allylic acetate products have been shown to be useful allyl nucleophile precursors through palladium-mediated reactions. These results suggest that acyloxyalkenyl bromides are efficient linchpins for multiple carbon−carbon bond formation.

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