Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)21628-21633
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number52
DOIs
Publication statusPublished - Dec 30 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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