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C–F Activation and hydrodefluorination of fluorinated alkenes at rhodium†
Daniel Noveski,Thomas Braun,Miriam Schulte,Beate Neumann,Hans-Georg Stammler
Dalton Transactions Pub Date : 09/22/2003 00:00:00 , DOI:10.1039/B306635E
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]CF(CF3)}(PEt3)3] (4) as well as Et3P(F){(Z)-CF[double bond, length as m-dash]CF(CF3)} (11). In contrast, addition of (E)-1,2,3,3,3-pentafluoropropene (8) to 9 yields [Rh{(E)-C(CF3)[double bond, length as m-dash]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.

Graphical abstract: C–F Activation and hydrodefluorination of fluorinated alkenes at rhodium
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