Your browser doesn't support javascript.
loading
Iron Corrole-Catalyzed Intramolecular Amination Reactions of Alkyl Azides. Spectroscopic Characterization and Reactivity of [FeV(Cor)(NAd)].
You, Tingjie; Shing, Ka-Pan; Wu, Liangliang; Wu, Kai; Wang, Hua-Hua; Liu, Yungen; Du, Lili; Liang, Runhui; Phillips, David Lee; Chang, Xiao-Yong; Huang, Jie-Sheng; Che, Chi-Ming.
Afiliación
  • You T; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Shing KP; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Wu L; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Wu K; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Wang HH; Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. China.
  • Liu Y; Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. China.
  • Du L; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Liang R; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Phillips DL; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Chang XY; Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. China.
  • Huang JS; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
  • Che CM; State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 000000, P. R. China.
Adv Sci (Weinh) ; 11(39): e2401420, 2024 Oct.
Article en En | MEDLINE | ID: mdl-39162002
ABSTRACT
As nitrogen analogues of iron-oxo species, high-valent iron-imido species have attracted great interest in the past decades. FeV-alkylimido species are generally considered to be key reaction intermediates in Fe(III)-catalyzed C(sp3)─H bond aminations of alkyl azides but remain underexplored. Here, it is reported that iron-corrole (Cor) complexes can catalyze a wide range of intramolecular C─H amination reactions of alkyl azides to afford a variety of 5-, 6- and 7-membered N-heterocycles, including alkaloids and natural product derivatives, with up to 3880 turnover numbers (TONs) and excellent diastereoselectivity (>991 d.r.). Mechanistic studies including density functional theory (DFT) calculations and intermolecular hydrogen atom abstraction (HAA) reactions reveal key reactive FeV-alkylimido intermediates. The [FeV(Cor)(NAd)] (Ad = adamantyl) complex is independently prepared and characterized through electron paramagnetic resonance (EPR), resonance Raman (rR) measurement, and X-ray photoelectron spectroscopy (XPS). This complex is reactive toward HAA reactions with kinetic isotope effects (KIEs) similar to [Fe(Cor)]-catalyzed intramolecular C─H amination of alkyl azides.
Palabras clave
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Adv Sci (Weinh) Año: 2024 Tipo del documento: Article Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Adv Sci (Weinh) Año: 2024 Tipo del documento: Article Pais de publicación: Alemania