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Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.
J Org Chem. 2019 07 05; 84(13):8589-8595.JO

Abstract

Olefin aziridination via organocatalytic nitrene transfer offers potential complementarity to metal-catalyzed methods; however there is a lack of reports of such reactions in the literature. Herein is reported a method that employs an iminium salt to catalyze the aziridination of styrenes by [ N-(p-toluenesulfonyl)imino]phenyliodinane (PhINTs). These reactions are hypothesized to proceed via a diaziridinium salt as the active oxidant. In addition to outlining the scope and limitations of the method, evidence for a polar, stepwise mechanism is presented, which provides new insight into the nature of iminium catalysis of nitrene transfer.

Authors+Show Affiliations

Department of Chemistry , University of Virginia , Charlottesville , Virginia 22904-4319 , United States.Department of Chemistry , University of Virginia , Charlottesville , Virginia 22904-4319 , United States.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

31173691

Citation

Johnson, Shea L., and Michael K. Hilinski. "Organocatalytic Olefin Aziridination Via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight." The Journal of Organic Chemistry, vol. 84, no. 13, 2019, pp. 8589-8595.
Johnson SL, Hilinski MK. Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight. J Org Chem. 2019;84(13):8589-8595.
Johnson, S. L., & Hilinski, M. K. (2019). Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight. The Journal of Organic Chemistry, 84(13), 8589-8595. https://doi.org/10.1021/acs.joc.9b01023
Johnson SL, Hilinski MK. Organocatalytic Olefin Aziridination Via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight. J Org Chem. 2019 07 5;84(13):8589-8595. PubMed PMID: 31173691.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight. AU - Johnson,Shea L, AU - Hilinski,Michael K, Y1 - 2019/06/19/ PY - 2019/6/8/pubmed PY - 2020/7/2/medline PY - 2019/6/8/entrez SP - 8589 EP - 8595 JF - The Journal of organic chemistry JO - J Org Chem VL - 84 IS - 13 N2 - Olefin aziridination via organocatalytic nitrene transfer offers potential complementarity to metal-catalyzed methods; however there is a lack of reports of such reactions in the literature. Herein is reported a method that employs an iminium salt to catalyze the aziridination of styrenes by [ N-(p-toluenesulfonyl)imino]phenyliodinane (PhINTs). These reactions are hypothesized to proceed via a diaziridinium salt as the active oxidant. In addition to outlining the scope and limitations of the method, evidence for a polar, stepwise mechanism is presented, which provides new insight into the nature of iminium catalysis of nitrene transfer. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/31173691/Organocatalytic_Olefin_Aziridination_via_Iminium_Catalyzed_Nitrene_Transfer:_Scope_Limitations_and_Mechanistic_Insight_ L2 - https://doi.org/10.1021/acs.joc.9b01023 DB - PRIME DP - Unbound Medicine ER -
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