Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N, O-acetals: Evidence for boronic acid assisted oxidative addition and an iminium activation pathway

Kevin T. Sylvester, Kevin Wu, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

Abstract

The mechanism of a recently reported Suzuki coupling reaction of quinoline-derived allylic N,O-acetals has been studied using a combination of structural, stereochemical, and kinetic isotope effect experiments. The data indicate that C-O activation is facilitated by Lewis acid assistance from the boronic acid coupling partner and an ionic SN1-like mechanism accounts for oxidative addition. In this context, we demonstrate the first direct observation of oxidative addition to a quinolinium salt. Notably, this mechanism is distinct from the more commonly described SN2(')-type oxidative addition of low-valent transition metals to most allylic electrophiles.

Original languageEnglish (US)
Pages (from-to)16967-16970
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number41
DOIs
StatePublished - Oct 17 2012

All Science Journal Classification (ASJC) codes

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

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