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Highly Stereospecific, Palladium-Catalyzed Cross-Coupling of Alkenylsilanols

Scott E. Denmark and Daniel Wehrli

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, Email: sdenmarkillinois.edu

S. E. Denmark, D. Wehrli, Org. Lett., 2000, 2, 565-568.

DOI: 10.1021/ol005565e (free Supporting Information)


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Abstract

E or Z-substituted alkenylsilanols are converted to disubstituted alkenes by a palladium(0)-catalyzed cross-coupling reaction with aryl or vinyl iodides in the presence of tetrabutylammonium fluoride or hydroxide. Yields and stereoselectivities are generally high, and the reaction is compatible with a wide range of functional groups.

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Key Words

Hiyama coupling


ID: J54-Y2000