Buchwald–Hartwig Amination and C–S/S–H Metathesis of Aryl Sulfides by Selective C–S Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Unified Mechanism for Activation of Inert C–S Bonds

Shiyi Yang, Xiang Yu, Albert Poater, Luigi Cavallo, Catherine S. J. Cazin, Steven P. Nolan, Michal Szostak

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

We report a combined experimental and mechanistic study on the Buchwald–Hartwig amination and C–S/S–H metathesis of aryl sulfides by selective activation of C–S bonds mediated by well-defined, air- and moisture-stable Pd(II)–NHC precatalysts, [Pd(NHC)(μ-Cl)Cl]2. This class of Pd(II)–NHC precatalysts displays excellent activity in the cross coupling of aryl sulfides. Most crucially, we unravel the unified mechanism for activation of C–S bonds in the C–N cross-coupling and C–S metathesis manifolds, where the inert C–S bond serves as a precursor to valuable amine or thioether products.
Original languageEnglish (US)
JournalOrganic Letters
DOIs
StatePublished - Dec 8 2022

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Fingerprint

Dive into the research topics of 'Buchwald–Hartwig Amination and C–S/S–H Metathesis of Aryl Sulfides by Selective C–S Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Unified Mechanism for Activation of Inert C–S Bonds'. Together they form a unique fingerprint.

Cite this