Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines

Thomas J.A. Graham, Jason D. Shields, Abigail Gutmann Doyle

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

A Ni(0) catalyst facilitates efficient C-C bond formation between a wide range of π-neutral and π-deficient aryl boronic acids and N-acyliminium precursors derived from quinoline and isoquinoline. The reaction proceeds under mild conditions and is tolerant of common organic functional groups. In addition, a simple one-pot protocol amenable to the direct use of substituted quinolines is described. Consistent with preliminary data revealing a mild, organoboronate-mediated racemization of enantioenriched N-acyliminium precursors, initial results indicate that a chiral phosphoramiditeligated nickel catalyst promotes enantioselective arylation of racemic substrate with no evidence of a kinetic resolution during catalysis.

Original languageEnglish (US)
Pages (from-to)980-984
Number of pages5
JournalChemical Science
Volume2
Issue number5
DOIs
StatePublished - May 9 2011

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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