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Iron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds

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... Full description

Journal Title: Chemistry: A European Journal June 2013, Vol.19(26), pp.8627-8633
Main Author: Cabrero-Antonino, Jose
Other Authors: Leyva-Perez, Antonio , Corma, Avelino
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201300386
Link: http://search.proquest.com/docview/1778021729/?pq-origsite=primo
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title: Iron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds
format: Article
creator:
  • Cabrero-Antonino, Jose
  • Leyva-Perez, Antonio
  • Corma, Avelino
subjects:
  • Alcohols
  • Alkynes
  • Thiols
  • Alkenes
  • Catalysts
  • Unsaturated
  • Arrays
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
  • Broensted Catalysis
  • Gold
  • Hydroaddition Reactions
  • Iron
  • Lewis Catalysis
ispartof: Chemistry: A European Journal, June 2013, Vol.19(26), pp.8627-8633
description: 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 Broensted triflimides has unveiled that iron(III) triflimide [Fe(NTf sub(2)) sub(3)] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh sub(3), readily decomposes at 80 degree C and releases triflimidic acid (HNTf sub(2)) that can catalyze the corresponding reaction, as shown by in situ super(19)F, super(15)N, and super(31)PNMR 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 Broensted...
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201300386
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleIron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds
creatorCabrero-Antonino, Jose ; Leyva-Perez, Antonio ; Corma, Avelino
contributorCabrero-Antonino, Jose (correspondence author)
ispartofChemistry: A European Journal, June 2013, Vol.19(26), pp.8627-8633
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subjectAlcohols ; Alkynes ; Thiols ; Alkenes ; Catalysts ; Unsaturated ; Arrays ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC) ; Broensted Catalysis ; Gold ; Hydroaddition Reactions ; Iron ; Lewis Catalysis
descriptionIn 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 Broensted triflimides has unveiled that iron(III) triflimide [Fe(NTf sub(2)) sub(3)] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh sub(3), readily decomposes at 80 degree C and releases triflimidic acid (HNTf sub(2)) that can catalyze the corresponding reaction, as shown by in situ super(19)F, super(15)N, and super(31)PNMR 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 Broensted...
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titleIron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds
descriptionIn 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 Broensted triflimides has unveiled that iron(III) triflimide [Fe(NTf sub(2)) sub(3)] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh sub(3), readily decomposes at 80 degree C and releases triflimidic acid (HNTf sub(2)) that can catalyze the corresponding reaction, as shown by in situ super(19)F, super(15)N, and super(31)PNMR 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 Broensted...
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titleIron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds
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abstractIn 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 Broensted triflimides has unveiled that iron(III) triflimide [Fe(NTf sub(2)) sub(3)] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh sub(3), readily decomposes at 80 degree C and releases triflimidic acid (HNTf sub(2)) that can catalyze the corresponding reaction, as shown by in situ super(19)F, super(15)N, and super(31)PNMR 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 Broensted...
doi10.1002/chem.201300386
urlhttp://search.proquest.com/docview/1778021729/
date2013-06-24