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Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.(CHEMISTRY)(Report)(Author abstract)

A major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [[([C.sub.6][F.sub.5]).sub.3]PF][B[([C.sub.6][F.sub.5]).sub.4]] 1 is shown to catal... Full description

Journal Title: Proceedings of the National Academy of Sciences of the United States July 29, 2014, Vol.111(30), p.10917(5)
Main Author: Perez, Manuel
Other Authors: Caputo, Christopher B. , Dobrovetsky, Roman , Stephan, Douglas W.
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0027-8424
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recordid: gale_ofa378680809
title: Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.(CHEMISTRY)(Report)(Author abstract)
format: Article
creator:
  • Perez, Manuel
  • Caputo, Christopher B.
  • Dobrovetsky, Roman
  • Stephan, Douglas W.
subjects:
  • Hydrogenation -- Methods
  • Alkenes -- Properties
  • Catalysis -- Methods
ispartof: Proceedings of the National Academy of Sciences of the United States, July 29, 2014, Vol.111(30), p.10917(5)
description: A major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [[([C.sub.6][F.sub.5]).sub.3]PF][B[([C.sub.6][F.sub.5]).sub.4]] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of [H.sub.2] (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations. fluorophosphonium www.pnas.org/cgi/doi/10.1073/pnas.1407484111
language: English
source:
identifier: ISSN: 0027-8424
fulltext: fulltext
issn:
  • 0027-8424
  • 00278424
url: Link


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titleMetal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.(CHEMISTRY)(Report)(Author abstract)
creatorPerez, Manuel ; Caputo, Christopher B. ; Dobrovetsky, Roman ; Stephan, Douglas W.
ispartofProceedings of the National Academy of Sciences of the United States, July 29, 2014, Vol.111(30), p.10917(5)
identifierISSN: 0027-8424
subjectHydrogenation -- Methods ; Alkenes -- Properties ; Catalysis -- Methods
descriptionA major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [[([C.sub.6][F.sub.5]).sub.3]PF][B[([C.sub.6][F.sub.5]).sub.4]] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of [H.sub.2] (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations. fluorophosphonium www.pnas.org/cgi/doi/10.1073/pnas.1407484111
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titleMetal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.(CHEMISTRY)(Report)(Author abstract)
descriptionA major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [[([C.sub.6][F.sub.5]).sub.3]PF][B[([C.sub.6][F.sub.5]).sub.4]] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of [H.sub.2] (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations. fluorophosphonium www.pnas.org/cgi/doi/10.1073/pnas.1407484111
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abstractA major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [[([C.sub.6][F.sub.5]).sub.3]PF][B[([C.sub.6][F.sub.5]).sub.4]] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of [H.sub.2] (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations. fluorophosphonium www.pnas.org/cgi/doi/10.1073/pnas.1407484111
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