"cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids

Liye Chen, Daniel R. Sanchez, Bufan Zhang, Brad P. Carrow

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd3-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.

Original languageEnglish (US)
Pages (from-to)12418-12421
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number36
DOIs
StatePublished - Jan 1 2017

All Science Journal Classification (ASJC) codes

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

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