Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight

[Image: see text] We report a room-temperature protocol for the hydrogenation of various amides to produce amines and alcohols. Compared with most previous reports for this transformation, which use high temperatures (typically, 100–200 °C) and H(2) pressures (10–100 bar), this system proceeds under...

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Autores principales: Kar, Sayan, Rauch, Michael, Kumar, Amit, Leitus, Gregory, Ben-David, Yehoshoa, Milstein, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7236134/
https://www.ncbi.nlm.nih.gov/pubmed/32455053
http://dx.doi.org/10.1021/acscatal.0c01406
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author Kar, Sayan
Rauch, Michael
Kumar, Amit
Leitus, Gregory
Ben-David, Yehoshoa
Milstein, David
author_facet Kar, Sayan
Rauch, Michael
Kumar, Amit
Leitus, Gregory
Ben-David, Yehoshoa
Milstein, David
author_sort Kar, Sayan
collection PubMed
description [Image: see text] We report a room-temperature protocol for the hydrogenation of various amides to produce amines and alcohols. Compared with most previous reports for this transformation, which use high temperatures (typically, 100–200 °C) and H(2) pressures (10–100 bar), this system proceeds under extremely mild conditions (RT, 5–10 bar of H(2)). The hydrogenation is catalyzed by well-defined ruthenium-PNNH pincer complexes (0.5 mol %) with potential dual modes of metal–ligand cooperation. An unusual Ru-amidate complex was formed and crystallographically characterized. Mechanistic investigations indicate that the room-temperature hydrogenation proceeds predominantly via the Ru–N amido/amine metal–ligand cooperation.
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spelling pubmed-72361342020-05-20 Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight Kar, Sayan Rauch, Michael Kumar, Amit Leitus, Gregory Ben-David, Yehoshoa Milstein, David ACS Catal [Image: see text] We report a room-temperature protocol for the hydrogenation of various amides to produce amines and alcohols. Compared with most previous reports for this transformation, which use high temperatures (typically, 100–200 °C) and H(2) pressures (10–100 bar), this system proceeds under extremely mild conditions (RT, 5–10 bar of H(2)). The hydrogenation is catalyzed by well-defined ruthenium-PNNH pincer complexes (0.5 mol %) with potential dual modes of metal–ligand cooperation. An unusual Ru-amidate complex was formed and crystallographically characterized. Mechanistic investigations indicate that the room-temperature hydrogenation proceeds predominantly via the Ru–N amido/amine metal–ligand cooperation. American Chemical Society 2020-04-21 2020-05-15 /pmc/articles/PMC7236134/ /pubmed/32455053 http://dx.doi.org/10.1021/acscatal.0c01406 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Kar, Sayan
Rauch, Michael
Kumar, Amit
Leitus, Gregory
Ben-David, Yehoshoa
Milstein, David
Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title_full Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title_fullStr Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title_full_unstemmed Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title_short Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
title_sort selective room-temperature hydrogenation of amides to amines and alcohols catalyzed by a ruthenium pincer complex and mechanistic insight
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7236134/
https://www.ncbi.nlm.nih.gov/pubmed/32455053
http://dx.doi.org/10.1021/acscatal.0c01406
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