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Selective Hydrodefluorination of Hexafluoropropene to Industrially Relevant Hydrofluoroolefins
Author(s) -
Phillips Nicholas A.,
White Andrew J. P.,
Crimmin Mark R.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900234
Subject(s) - chemistry , chemoselectivity , nucleophile , nucleophilic aromatic substitution , group (periodic table) , nucleophilic substitution , substitution reaction , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
The selective hydrodefluorination of hexafluoropropene to HFO‐1234ze and HFO‐1234yf can be achieved by reaction with simple group 13 hydrides of the form EH 3 ⋅ L (E=B, Al; L=SMe 2 , NMe 3 ). 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.