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. 2011 Jun 21;9(12):4545-9.
doi: 10.1039/c0ob01276a. Epub 2011 May 6.

Protolytic defluorination of trifluoromethyl-substituted arenes

Anila Kethe  1 , Adam F Tracy, Douglas A Klumpp
Affiliations

Protolytic defluorination of trifluoromethyl-substituted arenes

Anila Kethe et al. Org Biomol Chem. .

Abstract

A series of trifluoromethyl-substituted arenes were studied in their reactions with Brønsted superacids. The products from these reactions suggest the formation of reactive electrophiles, such as carbocations, acylium cations or equivalent electrophilic species. As such, Friedel-Crafts-type reactions occur between these species and arene nucleophiles. NMR studies were done, and the results suggest the formation of an acyl group from the trifluoromethyl groups in the superacid.

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Figures

Figure 1
Figure 1
13C NMR spectrum A: 3,5-bis(trifluoromethyl)benzoyl chloride (42) in FSO3H with d6-acetone external standard (labeled as *); 13C NMR spectrum B: 1,3,5-tris(trifluoromethyl) benzene (10) in FSO3H with d6-acetone external standard (labeled as *); peaks arising from unreacted 10 indicated by v designation).
Scheme 1
Scheme 1
Proposed mechanism for the conversion of 10 to 43 in FSO3H.
See this image and copyright information in PMC

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