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cis-Dihydroxylation of Unsaturated Potassium Alkyl- and Aryltrifluoroborates

Gary A. Molander* and Ruth Figueroa

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

G. A. Molander, R. Figueroa, Org. Lett., 2006, 8, 75-78.

DOI: 10.1021/ol052549e (free Supporting Information)


Abstract

The cis-dihydroxylation of olefin-containing potassium alkyl- and aryltrifluoroborates proceeds readily in moderate to excellent yields. The resulting diols are efficient coupling partners in Suzuki-Miyaura-type reactions with both alkenyl and aryl bromides.

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Key Words

Potassium alkyltrifluoroborates, Upjohn Dihydroxylation, N-methylmorpholine N-oxide, Osmium tetroxide


ID: J54-Y2006-190