Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters

Han Cao, Xuejing Liu, Fusheng Bie, Yijun Shi, Ying Han, Peng Yan, Michal Szostak, Chengwei Liu

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.

Original languageEnglish (US)
Pages (from-to)10829-10837
Number of pages9
JournalJournal of Organic Chemistry
Volume86
Issue number15
DOIs
StatePublished - Aug 6 2021

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters'. Together they form a unique fingerprint.

Cite this