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Synfacts 2008(1): 0075-0075  
DOI: 10.1055/s-2007-991437
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Trifluoromethylation of Salicyl Aldimines

Contributor(s): Paul Knochel, Tobias Thaler
A. D. Dilman*
N. D. Zelinsky Institute of Organic Chemistry and A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

An efficient synthetic route to the trifluoromethylation of C=N bonds with TMSCF3 is described. Hereby, the nitrogen atom does not have to be attached to an activating group. Intramolecular activation of the C=N bond is achieved by the formation of difluoroboron chelates. The reaction tolerates sensitive functionalities including nitro groups.