Stereoselective preparation of (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] and stereospecific synthesis of (E)-1,2-difluorostilbenes

Org Lett. 2002 May 2;4(9):1483-5. doi: 10.1021/ol025686+.

Abstract

[reaction: see text]. The novel bisstannane (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] 2 was stereoselectively prepared in a high overall yield through a sequential synthetic route from chlorotrifluoroethylene 1. The synthetic application of this novel bisstannane 2 was exemplified in the Pd(PPh3)4/CuI-catalyzed cross-coupling reactions with aryl iodides, yielding (E)-1,2-difluorostilbenes 3 in moderate to high yields.