Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

Jie Luo; Michael Rauch; Liat Avram; Yehoshoa Ben-David; David Milstein

doi:10.1021/jacs.0c10884

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

Jie Luo, Michael Rauch, Liat Avram, Yehoshoa Ben-David, David Milstein

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article › peer-review

Abstract

Direct hydrogenation of thioesters with H2 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.

Original language	English
Pages (from-to)	21628-21633
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	52
DOIs	https://doi.org/10.1021/jacs.0c10884
Publication status	Published - Dec 30 2020

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides",

abstract = "Direct hydrogenation of thioesters with H2 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. ",

author = "Jie Luo and Michael Rauch and Liat Avram and Yehoshoa Ben-David and David Milstein",

note = "Funding Information: This research was supported by the European Research Council (ERC AdG 692775). We thank Prof. Sergey Semenov and Dr. Yutao Sang for their help during the project. M.R. acknowledges the Zuckerman STEM Leadership Program for a research fellowship. D.M. is the Israel Matz Professorial Chair of Organic Chemistry.",

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AU - Luo, Jie

AU - Rauch, Michael

AU - Avram, Liat

AU - Ben-David, Yehoshoa

AU - Milstein, David

N1 - Funding Information: This research was supported by the European Research Council (ERC AdG 692775). We thank Prof. Sergey Semenov and Dr. Yutao Sang for their help during the project. M.R. acknowledges the Zuckerman STEM Leadership Program for a research fellowship. D.M. is the Israel Matz Professorial Chair of Organic Chemistry.

PY - 2020/12/30

Y1 - 2020/12/30

N2 - Direct hydrogenation of thioesters with H2 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.

AB - Direct hydrogenation of thioesters with H2 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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