Formation of thioesters by dehydrogenative coupling of thiols and alcohols with H2 evolution

Jie Luo, Michael Rauch, Liat Avram, Yael Diskin-Posner, Guy Shmul, Yehoshoa Ben-David, David Milstein

Research output: Contribution to journalArticle

Abstract

Thioesters play important roles in chemistry and biology, but their synthesis generally exhibits a poor atom economy and generates copious waste. We report here the dehydrogenative coupling of alcohols and thiols to yield thioesters and evolve H2. This waste-free reaction is catalysed by an acridine-based ruthenium pincer complex in hexamethyldisiloxane as the optimal solvent without any additives. Various thioesters were formed in good-to-excellent yields using equivalent amounts of alcohols and thiols in excellent selectivity with hydrogen gas as the only by-product. A plausible mechanism, which involves an outer-sphere dehydrogenation process in which the thiol not only serves as a reactant, but also as an assisting ligand, is proposed based on mechanistic studies and the isolation of intermediates. This system provides a facile, efficient and waste-free synthesis of thioesters. [Figure not available: see fulltext.]

Original languageEnglish
JournalNature Catalysis
DOIs
Publication statusAccepted/In press - 2020

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

Fingerprint Dive into the research topics of 'Formation of thioesters by dehydrogenative coupling of thiols and alcohols with H<sub>2</sub> evolution'. Together they form a unique fingerprint.

  • Cite this