Iron(III) triflimide as a catalytic substitute for gold(I) in hydroaddition reactions to unsaturated carbon-carbon bonds

摘要

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 C-C bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Br?nsted 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. Lewis and Br?nsted catalysis: It is shown that iron(III) catalyses as efficiently as gold(I) the hydroaddition of a wide array of nucleophiles, including water, alcohols, thiols, amines, alkynes, and alkenes, to multiple C-C bonds (see scheme).