Selective Cross-Coupling of Organic Halides with Allylic Acetates

Anka-Lufford, L., M. Prinsell, and D. Weix. Selective Cross-Coupling of Organic Halides With Allylic Acetates. J. Org. Chem., 2000.
Abstract A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.
Keywords alkyl-halidesaromatic halidesaryl halidesbromidescatalystcomplexesdirect insertiongrignard-reagentssubstitution-reactionzinc
DOI 10.1021/jo302086g