Mechanistic studies of the rhodium NHC catalyzed hydrodefluorination of polyfluorotoluenes

Leonid Schwartsburd, Mary F. Mahon, Rebecca C. Poulten, Mark R. Warren, Michael K. Whittlesey

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The six-membered-ring NHC complexes Rh(6-NHC)(PPh3)2H (6-NHC = 6-iPr (1), 6-Et (2), 6-Me (3)) have been employed in the catalytic hydrodefluorination (HDF) of C6F5CF3 and 2-C6F4HCF3. Stoichiometric studies showed that 1 reacted with C6F5CF3 at room temperature to afford cis- and trans-phosphine isomers of Rh(6-iPr)(PPh3)2F (4), which re-form 1 upon heating with Et3SiH. Although up to three consecutive HDF steps prove possible with C6F5CF3, the ultimate effectiveness of the catalysts is limited by their propensity to undergo C-H activation of partially fluorinated toluenes to give, for example, Rh(6-iPr)(PPh3)2(C6F4CF3) (7), which was isolated and structurally characterized.

Original languageEnglish
Pages (from-to)6165-6170
Number of pages6
Issue number21
Early online date8 Oct 2014
Publication statusPublished - 10 Nov 2014


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