Categories: C-Sn Bond Formation >
Synthesis of vinylstannanes
Recent Literature
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.
