Vinylzinc

Vinylzinc refers to organozinc compounds that contain a vinyl group bonded to a zinc atom. These compounds are valuable intermediates in organic synthesis, particularly for carbon-carbon bond formation reactions. The vinyl group can be attached to the zinc in various ways, such as through a direct carbon-zinc bond (R2Zn-CH=CHR') or in organozinc halides (RZnX-CH=CHR').

The preparation of vinylzinc reagents often involves the reaction of a vinyl halide with zinc metal, or through transmetalation reactions from other organometallic precursors. These reagents are known for their moderate reactivity and good functional group tolerance compared to more reactive organometallic species like Grignard reagents or organolithiums. This allows them to be used in the presence of various functional groups without undesired side reactions.

Vinylzinc compounds are commonly employed in cross-coupling reactions, such as the Negishi coupling, where they react with organic halides or pseudohalides in the presence of a palladium or nickel catalyst to form new carbon-carbon bonds. This is a powerful method for constructing complex organic molecules, including pharmaceuticals, natural products, and materials. Their ability to introduce a vinyl moiety into a molecule makes them particularly useful for creating alkenes and other unsaturated systems.