Synthesis of vinylstannanes

Recent Literature

A regio- and stereoselective magnesium-catalyzed hydrostannylation of internal and terminal alkynes provides the desired products with excellent yields and selectivities. A wide range of terminal and internal symmetrical and unsymmetrical alkynes can be converted using this alkaline earth metal catalyst as an effective alternative to transition metal catalysts.
M. Magre, M. Szewcyk, M. Rueping, Org. Lett., 2020, 22, 1594-1598.

Heterobimetallic (NHC)Cu-[MCO] catalysts enable the catalytic hydrostannylation of terminal alkynes with Bu₃SnH under mild conditions, with Markovnikov/anti-Markovnikov selectivity controlled by the Cu/M pairing. ^MeIMesCu-FeCp(CO)₂ as catalyst provides challenging α-vinylstannanes, whereas IMesCu-Mn(CO)₅ as catalyst provides (E)-β-vinylstannanes.
L.-J. Cheng, N. P. Mankad, J. Am. Chem. Soc., 2019, 141, 3710-3716.

Treatment of ketones with Bu₃SnLi followed by addition of MsCl/Et₃N to the resulting alkoxide provides vinylstannanes. Traces of Bu₃SnH in the crude reaction products could be removed by stirring in CHCl₃ with a catalytic amount of AIBN followed by filtration through silica gel.
A. Darwish, J. M. Chong, J. Org. Chem., 2007, 72, 1507-1509.

Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is controlled by the geometry of the double bond (Z- or syn-directing effect) rather than the nature of its substituents. Exclusively α-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.
A. Hamze, O. Provot, J.-D. Brion, M. Alami, J. Org. Chem., 2007, 72, 3868-3874.