Exploiting a "Beast" in Carbenoid Chemistry: Development of a Straightforward Direct Nucleophilic Fluoromethylation Strategy
Giovanna Parisi, Marco Colella, Serena Monticelli, Giuseppe Romanazzi, Wolfgang Holzer, Thierry Langer, Leonardo Degennaro, Vittorio Pace* and Renzo Luisi*
*Department of Pharmaceutical Chemistry, University of
Vienna, Althanstrasse 14, 1090 Vienna, Austria; Department of Pharmacy,
University of Bari, Via E. Orabona 4, 70125 Bari, Italy, Email: vittorio.pace
univie.ac.at,
renzo.luisiuniba.it
G. Parisi, M. Colella, S. Monticelli, G. Romanazzi, W. Holzer, T. Langer, L. Degennaro, V. Pace, R. Luisi, J. Am. Chem. Soc., 2017, 139, 13648-13651.
DOI: 10.1021/jacs.7b07891
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Abstract
A direct and straightforward nucleophilic fluoromethylation of organic compounds employs a very labile lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. The versatility of the strategy is showcased in reactions involving a plethora of electrophiles providing highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles in very good yields.
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Key Words
ID: J48-Y2017
