Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)

Tris(pentafluorophenyl)borane has been found to catalyze the two‐fold C(sp(3))−H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4‐silapiperidines in decent yields. The multi‐step reaction cascade involves amine‐to‐enamine dehydrogenation at two alky...

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Detalles Bibliográficos
Autores principales: Fang, Huaquan, Xie, Kaixue, Kemper, Sebastian, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048813/
https://www.ncbi.nlm.nih.gov/pubmed/33604987
http://dx.doi.org/10.1002/anie.202016664
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author Fang, Huaquan
Xie, Kaixue
Kemper, Sebastian
Oestreich, Martin
author_facet Fang, Huaquan
Xie, Kaixue
Kemper, Sebastian
Oestreich, Martin
author_sort Fang, Huaquan
collection PubMed
description Tris(pentafluorophenyl)borane has been found to catalyze the two‐fold C(sp(3))−H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4‐silapiperidines in decent yields. The multi‐step reaction cascade involves amine‐to‐enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter‐ and one intramolecular.
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spelling pubmed-80488132021-04-20 Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3) Fang, Huaquan Xie, Kaixue Kemper, Sebastian Oestreich, Martin Angew Chem Int Ed Engl Communications Tris(pentafluorophenyl)borane has been found to catalyze the two‐fold C(sp(3))−H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4‐silapiperidines in decent yields. The multi‐step reaction cascade involves amine‐to‐enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter‐ and one intramolecular. John Wiley and Sons Inc. 2021-03-03 2021-04-06 /pmc/articles/PMC8048813/ /pubmed/33604987 http://dx.doi.org/10.1002/anie.202016664 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Fang, Huaquan
Xie, Kaixue
Kemper, Sebastian
Oestreich, Martin
Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title_full Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title_fullStr Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title_full_unstemmed Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title_short Consecutive β,β′‐Selective C(sp(3))−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C(6)F(5))(3)
title_sort consecutive β,β′‐selective c(sp(3))−h silylation of tertiary amines with dihydrosilanes catalyzed by b(c(6)f(5))(3)
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048813/
https://www.ncbi.nlm.nih.gov/pubmed/33604987
http://dx.doi.org/10.1002/anie.202016664
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