Synfacts 2006(4): 0377-0377  
DOI: 10.1055/s-2006-934332
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Coupling of Aryl Bromides with Tetravinyltetrasiloxane

Contributor(s): Paul Knochel, Andrei Gavryushin
S. E. Denmark*, C. R. Butler
University of Illinois, Urbana, USA
Further Information

Publication History

Publication Date:
24 March 2006 (online)

Significance

Substituted styrenes and vinyl-substituted heterocycles are important intermediates in organic synthesis. The present protocol offers a general approach to this class of compounds that starts from readily available aryl or hetaryl halides and inexpensive oligomeric vinylsiloxane. A variety of functional groups, including ester, nitro, ketone and hydroxyl are perfectly tolerated. The reaction proceeds under mild conditions and affords the products in high yields. Even sterically hindered substrates like bromomesitylene can be successfully used in the process.