Bu3SnCHCH2

Bu3SnCHCH2, often written as Bu3SnCH=CH2, is a vinyltributyltin compound. It is an organotin reagent in which a tributyltin group (Bu3Sn) is bonded to a vinyl carbon, giving the vinylstannane structure Bu3Sn–CH=CH2. The compound has a relatively low polarity and typically appears as a colorless liquid or pale oil at room temperature. Its molecular formula is C14H30Sn and its approximate molecular weight is 317 g/mol.

Preparation and related methods

Bu3SnCH=CH2 can be prepared by hydrostannylation of acetylene (C2H2) with tributyltin hydride (Bu3SnH) under radical conditions, delivering the vinylstannane in a single step. Alternative routes include transmetalation or coupling strategies starting from vinyl halides or vinyl boranes, using Bu3SnCl or related reagents under appropriate conditions. The choice of method depends on the desired scale and functional-group tolerance.

Reactivity and applications

Vinyltributyltin compounds are important building blocks in organic synthesis, particularly as partners in Stille cross-coupling reactions. In the presence of palladium catalysts, the Bu3Sn group undergoes transmetalation to form vinyl–Pd intermediates that couple with aryl or vinyl electrophiles to give substituted alkenes. This enables installation of vinyl groups into complex molecules with good stereochemical control. Vinylstannanes also participate in various radical and cyclization sequences in modern synthetic strategies.

Safety and handling

Organotin compounds can be toxic and may pose environmental hazards. Bu3SnCH=CH2 should be handled with appropriate precautions to avoid ingestion, inhalation, or skin contact. Waste disposal should follow applicable regulations for organotin compounds.

See also

Vinylstannanes, Stille coupling, tributylstannane, Bu3SnH.