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Stereospecific Suzuki Cross-Coupling of Alkyl α-Cyanohydrin Triflates

Anyu He and J. R. Falck*

*Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, Email: j.falckutsouthwestern.edu

A. He, J. R. Falck, J. Am. Chem. Soc., 2010, 132, 2524-2525.

DOI: 10.1021/ja910582n (free Supporting Information)


Abstract

α-Cyanohydrin triflates undergo Pd-catalyzed cross-coupling with aryl and vinyl boronic acids under mild conditions. Coupling proceeds with complete inversion of configuration at the stereogenic carbon. The resultant nitrile can be easily converted into a variety of alternative functional groups of value in organic synthesis and thus a high level of molecular diversity can be achieved.

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Key Words

Nitriles, α-Arylation


ID: J48-Y2010-0700