Copper catalyzed Heck-like cyclizations of oxime esters

Adele Faulkner, Nicholas J. Race, James S. Scott, John F. Bower*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

96 Citations (Scopus)
210 Downloads (Pure)

Abstract

Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds via the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed via oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants. This journal is

Original languageEnglish
Pages (from-to)2416-2421
Number of pages6
JournalChemical Science
Volume5
Issue number6
Early online date9 Apr 2014
DOIs
Publication statusPublished - 1 Jun 2014

Structured keywords

  • BCS and TECS CDTs

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  • Projects

    New Transition Metal Catalysed Methods for Alkyl C-N Bond Formation

    Bower, J. F.

    3/11/113/11/13

    Project: Research

    Cite this

    Faulkner, A., Race, N. J., Scott, J. S., & Bower, J. F. (2014). Copper catalyzed Heck-like cyclizations of oxime esters. Chemical Science, 5(6), 2416-2421. https://doi.org/10.1039/c4sc00652f