Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

ABSTRACT

α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C-H zincation and copper-catalyzed C(sp3 )-C(sp2 ) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of ß,γ-unsaturated carbonyl compounds.