1549641-61-3Relevant academic research and scientific papers
Elevated catalytic activity of ruthenium(II)-porphyrin-catalyzed carbene/nitrene transfer and insertion reactions with n-heterocyclic carbene ligands
Chan, Ka-Ho,Guan, Xiangguo,Lo, Vanessa Kar-Yan,Che, Chi-Ming
, p. 2982 - 2987 (2014)
Bis(NHC)ruthenium(II)-porphyrin complexes were designed, synthesized, and characterized. Owing to the strong donor strength of axial NHC ligands in stabilizing the trans Mi￡CRR′/Mi￡NR moiety, these complexes showed unprecedently high catalytic activity towards alkene cyclopropanation, carbene C-H, N-H, S-H, and O-H insertion, alkene aziridination, and nitrene C-H insertion with turnover frequencies up to 1950 min-1. The use of chiral [Ru(D4-Por)(BIMe)2] (1 g) as a catalyst led to highly enantioselective carbene/nitrene transfer and insertion reactions with up to 98 % ee. Carbene modification of the N terminus of peptides at 37 °C was possible. DFT calculations revealed that the trans axial NHC ligand facilitates the decomposition of diazo compounds by stabilizing the metal-carbene reaction intermediate.
Iron porphyrin catalysed light driven C-H bond amination and alkene aziridination with organic azides
Che, Chi-Ming,Du, Yi-Dan,To, Wai-Pong,Wang, Hai-Xu,Zhou, Cong-Ying
, p. 4680 - 4686 (2020/06/18)
Visible light driven nitrene transfer and insertion reactions of organic azides are an attractive strategy for the design of C-N bond formation reactions under mild reaction conditions, the challenge being lack of selectivity as a free nitrene reactive intermediate is usually involved. Herein is described an iron(iii) porphyrin catalysed sp3 C-H amination and alkene aziridination with selectivity by using organic azides as the nitrogen source under blue LED light (469 nm) irradiation. The photochemical reactions display chemo- and regio-selectivity and are effective for the late-stage functionalization of natural and bioactive compounds with complexity. Mechanistic studies revealed that iron porphyrin plays a dual role as a photosensitizer and as a catalyst giving rise to a reactive iron-nitrene intermediate for subsequent C-N bond formation.
An Effective [FeIII(TF4DMAP)Cl] Catalyst for C-H Bond Amination with Aryl and Alkyl Azides
Du, Yi-Dan,Xu, Zhen-Jiang,Zhou, Cong-Ying,Che, Chi-Ming
supporting information, p. 895 - 899 (2019/02/14)
[FeIII(TF4DMAP)Cl] can efficiently catalyze intermolecular sp3 C-H amination using aryl azides and intramolecular sp3 C-H amination of alkyl azides in moderate-to-high product yields. At catalyst loading down to 1 mol %, the reactions display high chemo- and regioselectivity with broad substrate scope and are effective for late-stage functionalization of complex natural/bioactive molecules.
