New mechanistic insights into the copper catalyzed ring expansion of vinyl aziridines: Evidence in support of a copper(i) mediated pathway

Daniel J. MacK, Jon T. Njardarson

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

We report how mechanistically inspired metal additive choices result in acceleration of the copper catalyzed vinyl aziridine ring expansion reaction. Most importantly, we demonstrate how the use of in situ reducing agents significantly accelerates the reaction, suggesting a copper(i) active species. These acceleration results were confirmed using Cu(hfacac)(cod) as catalyst. NMR kinetic studies revealed the relative importance of olefin and sulfonamide electronics on the reaction rate and established the order of both catalyst and substrate, which together favored a new copper(i) insertion mechanism.

Original languageEnglish (US)
Pages (from-to)3321-3325
Number of pages5
JournalChemical Science
Volume3
Issue number11
DOIs
StatePublished - Nov 1 2012

ASJC Scopus subject areas

  • Chemistry(all)

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