Advanced Synthesis & Catalysis | 2019
Selective hydrodefluorination of hexafluoropropene to industrially relevant hydrofluoroolefins
Abstract
The selective hydrodefluorination of hexafluoropropene to HFO-1234ze and HFO-1234yf can be achieved by reaction with simple group 13 hydrides of the form EH3•L (E = B, Al; L = SMe2, NMe3). The chemoselectivity varies depending on the nature of the group 13 element. A combination of experiments and DFT calculations show that competitive nucleophilic vinylic substitution and addition-elimination mechanisms involving hydroborated intermediates lead to complementary selectivities.