C–F Activation and hydrodefluorination of fluorinated alkenes at rhodium†
Abstract
Reaction of [RhH(PEt3)4]
(9) with hexafluoropropene (1) affords the C–F activation product [Rh{(Z)-CF![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
CF(CF3)}(PEt3)3]
(4) as well as Et3P(F){(Z)-CFCF(CF3)}
(11). In contrast, addition of (E)-1,2,3,3,3-pentafluoropropene (8) to 9 yields [Rh{(E)-C(CF3)CHF}(PEt3)3]
(12) together with [RhF(PEt3)3]
(6) and (Z)-1,3,3,3-tetrafluoropropene (10). Treatment of 12 with hydrogen effects the formation of 1,1,1-trifluoropropane (2) and the fluoro compounds [RhF(PEt3)3]
(6) and cis-mer-[Rh(H)2F(PEt3)3]
(7). On treatment of 6 or of a mixture of 6 and 7 with HSiPh3 the complexes [RhH(PEt3)3]
(3) and cis-fac-[Rh(H)2(SiPh3)(PEt3)3]
(13) are obtained. Both compounds are capable of the C–F activation of hexafluoropropene (1) to afford 4. The molecular structure of complex 13 has been determined by X-ray crystallography.
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