101000

Ethynyltributylstannane

Palladium catalyzed cross-coupling reaction is an important route to introduce unsaturation in a molecule, and ethynyltributylstannane is often used. In this manner, unsymme-trically 3,4-disubstituted thiophenes were prepared (Scheme 1) (1).

 

The particular reactivity of ethynyltributyl-stannane is illustrated in Scheme 2: the normal regioselectivity of benzannulation reaction observed with alkynes or silylated derivatives can be reversed by the use of stannylated derivatives
(2).

 

Ethynyltributylstannane is a precursor of ethynylarsines, themelves used in the preparation of the first simple arsaalkynes (Scheme 3) (3).

 

 

References:

(1)	X.-S. Ye , H. N. C. Wong J. Org. Chem. 1997, 62, 1940.
(2)	S. Chamberlin, M. L. Waters, W. D. Wulff J. Am. Chem. Soc., 1994, 116, 3113.
(3)	J.-C. Guillemin, L. Lassalle, P. Dréan, G. Wlodarczak, J. Demaison J. Am. Chem. Soc., 1994, 116, 8930.