Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: The missing link

Andy A. Thomas, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

Despite the widespread application of Suzuki-Miyaura cross-coupling to forge carbon-carbon bonds, the structure of the reactive intermediates underlying the key transmetalation step from the boron reagent to the palladium catalyst remains uncertain. Here we report the use of low-temperature rapid injection nuclear magnetic resonance spectroscopy and kinetic studies to generate, observe, and characterize these previously elusive complexes. Specifically, this work establishes the identity of three different species containing palladium-oxygen-boron linkages, a tricoordinate boronic acid complex, and two tetracoordinate boronate complexes with 2:1 and 1:1 stoichiometry with respect to palladium. All of these species transfer their boron-bearing aryl groups to a coordinatively unsaturated palladium center in the critical transmetalation event.

Original languageEnglish (US)
Pages (from-to)329-332
Number of pages4
JournalScience
Volume352
Issue number6283
DOIs
StatePublished - Apr 15 2016

ASJC Scopus subject areas

  • General

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