102060

Vinyltributylstannane

Vinyltributylstannane is an efficient reagent in the Stille coupling. The preparation of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via a reaction between halovinylsulfoxides and vinylstannane (Scheme 1) (1).

 

The Stille reaction has also been investigated on solid phase synthesis for the preparation of dienes by coupling vinylstannane with a-unsaturated halides on polystyrene support (Scheme 2) (2).

 

The use of vinyltributylstannane can lead to the synthesis of unsaturated heterocompounds as boron, arsenious or antimony derivatives (Scheme 3) (3).

 

 

References:
(1) R. S. Paley, A. de Dios, L. A. Estroff, J. A. Lafontaine, C. Montero, D. J. Mc Culley, M. B. Rubio, M. P. Ventura, H. L. Weers J. Org. Chem. ,1997, 62, 6326.
(2) M. A. Blaskovich, M. Kahn J. Org. Chem. ,1998, 63, 1119.
(3) L. Lassalle, J.-C. Guillemin Organometallics, 1994, 13, 1525.