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Synthesis of Functionalized Organotrifluoroborates via Halomethyltrifluoroborates

Gary A. Molander* and Jungyeob Ham

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

G. A. Molander, J. Ham, Org. Lett., 2006, 8, 2031-2034.

DOI: 10.1021/ol060375a (free Supporting Information)


Abstract

A new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of potassium bromo- and iodomethyltrifluoroborates is described. Potassium halomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF2.

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Key Words

potassium trifluoroborates, amines, ethers, sulfides


ID: J54-Y2006-1240