Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides

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Abstract

We report here cobalt-N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary alkyl halides suggest that the present reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing and cycloalkyl groups.

Original languageEnglish
Pages (from-to)9279-9282
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number25
DOIs
Publication statusPublished - 2013 Jun 26
Externally publishedYes

ASJC Scopus subject areas

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

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