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Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

[Image: see text] Direct hydrogenation of thioesters with H(2) provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we repor...

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Autores principales: Luo, Jie, Rauch, Michael, Avram, Liat, 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/PMC7775745/
https://www.ncbi.nlm.nih.gov/pubmed/33332968
http://dx.doi.org/10.1021/jacs.0c10884
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author Luo, Jie
Rauch, Michael
Avram, Liat
Ben-David, Yehoshoa
Milstein, David
author_facet Luo, Jie
Rauch, Michael
Avram, Liat
Ben-David, Yehoshoa
Milstein, David
author_sort Luo, Jie
collection PubMed
description [Image: see text] Direct hydrogenation of thioesters with H(2) provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
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spelling pubmed-77757452021-01-04 Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides Luo, Jie Rauch, Michael Avram, Liat Ben-David, Yehoshoa Milstein, David J Am Chem Soc [Image: see text] Direct hydrogenation of thioesters with H(2) provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds. American Chemical Society 2020-12-17 2020-12-30 /pmc/articles/PMC7775745/ /pubmed/33332968 http://dx.doi.org/10.1021/jacs.0c10884 Text en © 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 Luo, Jie
Rauch, Michael
Avram, Liat
Ben-David, Yehoshoa
Milstein, David
Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title_full Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title_fullStr Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title_full_unstemmed Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title_short Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
title_sort catalytic hydrogenation of thioesters, thiocarbamates, and thioamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7775745/
https://www.ncbi.nlm.nih.gov/pubmed/33332968
http://dx.doi.org/10.1021/jacs.0c10884
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