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Reagents for Fluorination

Aldrich ChemFiles 2007, 7.1, 11.

Nucleophilic Trifluoromethylation

The trifluoromethyl substituent has long been recognized for the positive influence it can have on the biological activity of molecules. Professor William Dolbier, Jr. (University of Florida) has developed numerous trifluoromethylation reactions using CF3I in the presence of a powerful two-electron reductant, tetrakis(dimethylamino)ethylene (TDAE), to generate a nucleophilic trifluoromethyl anion. In many cases, the CF3I/TDAE reagent system is compares well to TMSCF3 (Ruppert’s reagent), a reagent popularized by the Prakash group and others.1 The reagent system has shown tremendous promise in the nucleophilic trifluoromethylation of: aldehydes and ketones,2 imines,3 disulfides and diselenides,4 as well as cyclic sulfates.5

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  1. Prakash, G. K. S.; Mandal, M. J. Am. Chem. Soc. 2002, 124, 6538.
  2. (a) Pooput, C. et al. J. Org. Chem. 2006, 71, 3564. (b) Aït-Mohand, S. et al. Org. Lett. 2001, 3, 4271.
  3. Xu, W.; Dolbier, W. R., Jr. J. Org. Chem. 2005, 70, 4741.
  4. Pooput, C. et al. Org. Lett. 2004, 6, 301.
  5. Takechi, N. et al. Org. Lett. 2002, 4, 4671.

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