FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6‐tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ‐terpinene as a dihydrogen surrogate. A va...

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Autores principales: Khan, Imtiaz, Reed‐Berendt, Benjamin G., Melen, Rebecca L., Morrill, Louis C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6207922/
https://www.ncbi.nlm.nih.gov/pubmed/30106498
http://dx.doi.org/10.1002/anie.201808800
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author Khan, Imtiaz
Reed‐Berendt, Benjamin G.
Melen, Rebecca L.
Morrill, Louis C.
author_facet Khan, Imtiaz
Reed‐Berendt, Benjamin G.
Melen, Rebecca L.
Morrill, Louis C.
author_sort Khan, Imtiaz
collection PubMed
description Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6‐tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ‐terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).
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spelling pubmed-62079222018-11-06 FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers Khan, Imtiaz Reed‐Berendt, Benjamin G. Melen, Rebecca L. Morrill, Louis C. Angew Chem Int Ed Engl Communications Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6‐tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ‐terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield). John Wiley and Sons Inc. 2018-08-24 2018-09-17 /pmc/articles/PMC6207922/ /pubmed/30106498 http://dx.doi.org/10.1002/anie.201808800 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://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
Khan, Imtiaz
Reed‐Berendt, Benjamin G.
Melen, Rebecca L.
Morrill, Louis C.
FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title_full FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title_fullStr FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title_full_unstemmed FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title_short FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
title_sort flp‐catalyzed transfer hydrogenation of silyl enol ethers
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6207922/
https://www.ncbi.nlm.nih.gov/pubmed/30106498
http://dx.doi.org/10.1002/anie.201808800
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