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Development of the Suzuki-Miyaura Cross-Coupling Reaction: Use of Air-Stable Potassium Alkynyltrifluoroborates in Aryl Alkynylations

Gary A. Molander*, Bryson W. Katona and Fouzia Machrouhi

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, Email: gmolandrsas.upenn.edu

G. A. Molander, B. W. Katona, F. Machrouhi, J. Org. Chem., 2002, 67, 8416-8423.

DOI: 10.1021/jo0262356 (free Supporting Information)


Abstract

The palladium-catalyzed cross-coupling reaction of potassium alkynyltrifluoroborates with aryl halides or triflates proceeds readily with moderate to excellent yields. The potassium alkynyltrifluoroborates are air- and moisture-stable crystalline solids that can be stored indefinitely, which will provide an advantage in applications to combinatorial chemistry.

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Key Words

Potassium Alkynyltrifluoroborates, Suzuki Coupling, Alkynylation


ID: J42-Y2002-220