Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides

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12 Citations (Scopus)

Abstract

A cobalt-N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with olefins as alkylating agents that we developed previously. Stereochemical outcomes of secondary alkylation reactions suggest that the 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 group and the cycloalkyl groups.

Original languageEnglish
Pages (from-to)419-424
Number of pages6
JournalPure and Applied Chemistry
Volume86
Issue number3
DOIs
Publication statusPublished - 2014 Mar 20
Externally publishedYes

Keywords

  • alkylation
  • C-H functionalization
  • cobalt
  • imines

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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