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Iron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon–Carbon Bonds
Author(s) -
CabreroAntonino Jose R.,
LeyvaPérez Antonio,
Corma Avelino
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300386
Subject(s) - catalysis , chemistry , nucleophile , carbon fibers , selectivity , organic chemistry , polymer chemistry , medicinal chemistry , materials science , composite number , composite material
In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple CC bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Brønsted triflimides has unveiled that iron(III) triflimide [Fe(NTf 2 ) 3 ] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh 3 , readily decomposes at 80 °C and releases triflimidic acid (HNTf 2 ) that can catalyze the corresponding reaction, as shown by in situ 19 F, 15 N, and 31 P NMR spectroscopy. The results presented here demonstrate that each of the two catalyst types has weaknesses and strengths and complement each other. Iron(III) triflimide can act as a substitute of gold(I) triflimide as a catalyst for hydroaddition reactions to unsaturated carbon–carbon bonds.