Copper-Mediated Cross-Dehydrogenative Coupling of 2-Methylpyridine and 8-Methylquinoline with Methyl Ketones and Benzamides

Gadde Sathish Kumar, Joshua William Boyle, Ciputra Tejo, Philip Wai Hong Chan

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7 Citations (Scopus)

Abstract

A synthetic method to prepare (E)-(pyridin-2-yl)enones and (E)-(quinolin-8-yl)enones that relies on the respective copper(I)-catalyzed formal cross-dehydrogenative coupling (CDC) reaction of 2-methylpyridine and 8-methylquinoline with methyl ketones has been discovered. The mechanism was delineated to follow a pathway involving oxidation of the N-heterocycle to its corresponding aldehyde adduct prior to reaction with the methyl ketone. The versatility and substrate dependent divergence in the reactivity of the copper-mediated CDC strategy was exemplified by its application to the synthesis of N-(quinolin-8-ylmethyl)amide and N-(quinolin-8-ylmethyl)aniline adducts on switching the cross-coupling partner to benzamides or an aniline derivative.

Original languageEnglish
Pages (from-to)385-389
Number of pages5
JournalChemistry-An Asian Journal
Volume11
Issue number3
DOIs
Publication statusPublished - 4 Feb 2016

Keywords

  • C-H bond activation
  • copper
  • cross-dehydrogenative coupling
  • homogeneous catalysis
  • synthetic methods

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