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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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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. |
format | Online Article Text |
id | pubmed-7775745 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
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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