Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement

Selina C. Wang, Dawn M. Troast, Martin Conda Sheridan, Gang Zuo, Donna LaGarde, Janis Louie, Dean J. Tantillo

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane- cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/ reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

Original languageEnglish (US)
Pages (from-to)7822-7833
Number of pages12
JournalJournal of Organic Chemistry
Volume74
Issue number20
DOIs
StatePublished - Oct 16 2009

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Cyclopentanes
Ligands
Catalysts
Substrates
Experiments
carbene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Wang, S. C., Troast, D. M., Conda Sheridan, M., Zuo, G., LaGarde, D., Louie, J., & Tantillo, D. J. (2009). Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement. Journal of Organic Chemistry, 74(20), 7822-7833. https://doi.org/10.1021/jo901525u

Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement. / Wang, Selina C.; Troast, Dawn M.; Conda Sheridan, Martin; Zuo, Gang; LaGarde, Donna; Louie, Janis; Tantillo, Dean J.

In: Journal of Organic Chemistry, Vol. 74, No. 20, 16.10.2009, p. 7822-7833.

Research output: Contribution to journalArticle

Wang, SC, Troast, DM, Conda Sheridan, M, Zuo, G, LaGarde, D, Louie, J & Tantillo, DJ 2009, 'Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement', Journal of Organic Chemistry, vol. 74, no. 20, pp. 7822-7833. https://doi.org/10.1021/jo901525u
Wang, Selina C. ; Troast, Dawn M. ; Conda Sheridan, Martin ; Zuo, Gang ; LaGarde, Donna ; Louie, Janis ; Tantillo, Dean J. / Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 20. pp. 7822-7833.
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