Platinum Catalysed Hydrostannylation of Terminal Alkynes; Highly Selective Synthesis of Vinyl Stannanes

We present the first study on the application of platinum complexes in the hydrostannylation of terminal alkynes. A range of platinum complexes were screened, with PtCl2/XPhos proving to provide the best selectivity for the beta-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

Automated summary

We have conducted the first study on the use of platinum complexes in the hydrostannylation of terminal alkynes. Among several platinum complexes screened, PtCl2/XPhos exhibited the highest selectivity for beta-(E)-vinyl stannane. The catalyst system not only provided superior selectivity compared to palladium catalysis but also allowed for a telescoped hydrometallation/cross-coupling sequence, eliminating the need for excessive manipulation or purification of the intermediate stannane.