Pd-PEPPSI: Water-Assisted Suzuki−Miyaura Cross-Coupling of Aryl Esters at Room Temperature using a Practical Palladium-NHC (NHC=N-Heterocyclic Carbene) Precatalyst

Guangchen Li, Shicheng Shi, Peng Lei, Michal Szostak

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

A Pd-PEPPSI-catalyzed (Pd=Palladium, PEPPSI=pyridine-enhanced precatalyst preparation stabilization and initiation) Suzuki-Miyaura cross-coupling of aryl esters via selective C−O cleavage at room temperature is reported. The developed catalyst system displays broad substrate scope with respect to both components under practical ambient reaction conditions using readily-available, cheap, modular, air- and moisture-stable Pd-NHC precatalyst (NHC=N-heterocyclic carbene). The use of water proved crucial for achieving high reactivity in this coupling. The catalyst system represents the mildest conditions for the Suzuki−Miyaura cross-coupling of aryl esters reported to date. The protocol also allowed for achieving TON >1,000 (TON=turnover number) in the Suzuki−Miyaura ester coupling for the first time. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)1538-1543
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number7
DOIs
StatePublished - Apr 3 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • C−O activation
  • Pd-PEPPSI
  • Suzuki−Miyaura
  • aryl esters
  • cross-coupling

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