Probing the electronic demands of transmetalation in the palladium-catalyzed cross-coupling of arylsilanolates

Scott E. Denmark, Russell C. Smith, Wen Tau T. Chang

Research output: Contribution to journalArticle

Abstract

The electronic characteristics of coupling partners in the transmetalation step for the cross-coupling reaction of arylsilanolates have been investigated. The ability to interrogate the transmetalation event by in situ preparation of the arylpalladium(II) silanolate intermediate has enabled a Hammett analysis for both the aryl electrophile and arylsilanolate to be conducted. These studies reveal that electron-donating groups on the silicon nucleophile and electron-withdrawing groups on the electrophile accelerate the transmetalation process.

Original languageEnglish (US)
Pages (from-to)4391-4396
Number of pages6
JournalTetrahedron
Volume67
Issue number24
DOIs
StatePublished - Jun 17 2011

Keywords

  • Cross-coupling
  • Hammett relationship
  • Mechanism
  • Organosilicon
  • Transmetalation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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