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A General Method for Imine Formation Using B(OCH2CF3)3

Jonathan T. Reeves*, Michael D. Visco, Maurice A. Marsini, Nelu Grinberg, Carl A. Busacca, Anita E. Mattson and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email:

J. T. Reeves, M. D. Visco, M. A. Marsini, N. Grinberg, C. A. Busacca, A. E. Mattson, C. H. Senanayake, Org. Lett., 2015, 17, 2442-2445.

DOI: 10.1021/acs.orglett.5b00949 (free Supporting Information)

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Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] is a mild and general reagent for condensation of amides or amines with carbonyl compounds providing N-Sulfinyl, N-toluenesulfonyl, N-(dimethylamino)sulfamoyl, N-diphenylphosphinoyl, N-(α-methylbenzyl), and N-(4-methoxyphenyl) aldimines at room temperature. The reactions are operationally simple, and the products are obtained without special workup or isolation procedures.

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Key Words

imines, N-sulfinyl imines, N-sulfonyl imines

ID: J54-Y2015