Directed nickel-catalyzed negishi cross coupling of alkyl aziridines

Daniel K. Nielsen, Chung Yang Huang, Abigail Gutmann Doyle

Research output: Contribution to journalArticle

65 Scopus citations

Abstract

Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp3-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition and facilitates reductive elimination. Studies pertinent to elucidation of the mechanism of cross coupling are also presented.

Original languageEnglish (US)
Pages (from-to)13605-13609
Number of pages5
JournalJournal of the American Chemical Society
Volume135
Issue number36
DOIs
StatePublished - Sep 11 2013

All Science Journal Classification (ASJC) codes

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

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