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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.

SUBMITTER: Luo J

PROVIDER: S-EPMC7775745 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides.

Luo Jie J Rauch Michael M Avram Liat L Ben-David Yehoshoa Y Milstein David D

Journal of the American Chemical Society 20201217 52

Direct hydrogenation of thioesters with H<sub>2</sub> 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 alc ...[more]

PMID: 33332968

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