149552-43-2Relevant articles and documents
Expedient Synthesis of 2-Iminothiazolidines via Telescoping Reactions Including Iron-Catalyzed Nitrene Transfer and Domino Ring-Opening Cyclization (DROC)
Coin, Guillaume,de Ferrier de Montal, Oriane,Dubourdeaux, Patrick,Latour, Jean-Marc
, p. 443 - 448 (2021)
2-iminothiazolidines are important scaffold for pharmaceutical drugs. Herein, we describe a fast and easy procedure for their synthesis by a telescoping reaction integrating an iron-catalyzed nitrene transfer under mild conditions. The aziridination react
Catalytic asymmetric heterogeneous aziridination of styrene using Cu 2+ -exchanged zeolite Y: Effect of the counter-cation on enantioselectivity and on the reaction profile
Gullick, John,Ryan, Darragh,McMorn, Paul,Bethell, Donald,King, Frank,Hancock, Frederick,Hutchings, Graham
, p. 1470 - 1478 (2004)
Effective catalysts have Cu2+ -exchange levels of ca. 40-60% of the maximum concentration for electroneutrality and, consequently, Cu-zeolite Y catalysts contain an additional counter-cation (H+, Li-, Na+, Ksup
Ligand Redox Noninnocence in [CoIII(TAML)]0/- Complexes Affects Nitrene Formation
De Bruin, Bas,Oudsen, Jean-Pierre H.,Rietdijk, Niels R.,Siegler, Maxime A.,Tepaske, Martijn A.,Tromp, Moniek,Van Der Vlugt, Jarl Ivar,Van Leest, Nicolaas P.,Venderbosch, Bas
supporting information, p. 552 - 563 (2020/02/20)
The redox noninnocence of the TAML scaffold in cobalt-TAML (tetra-amido macrocyclic ligand) complexes has been under debate since 2006. In this work, we demonstrate with a variety of spectroscopic measurements that the TAML backbone in the anionic complex [CoIII(TAMLred)]- is truly redox noninnocent and that one-electron oxidation affords [CoIII(TAMLsq)]. Multireference (CASSCF) calculations show that the electronic structure of [CoIII(TAMLsq)] is best described as an intermediate spin (S = 1) cobalt(III) center that is antiferromagnetically coupled to a ligand-centered radical, affording an overall doublet (S = 1/2) ground-state. Reaction of the cobalt(III)-TAML complexes with PhINNs as a nitrene precursor leads to TAML-centered oxidation and produces nitrene radical complexes without oxidation of the metal ion. The ligand redox state (TAMLred or TAMLsq) determines whether mono-or bis-nitrene radical complexes are formed. Reaction of [CoIII(TAMLsq)] or [CoIII(TAMLred)]- with PhINNs results in the formation of [CoIII(TAMLq)(Na￠Ns)] and [CoIII(TAMLq)(Na￠Ns)2]-, respectively. Herein, ligand-to-substrate single-electron transfer results in one-electron-reduced Fischer-type nitrene radicals (Na￠Ns-) that are intermediates in catalytic nitrene transfer to styrene. These nitrene radical species were characterized by EPR, XANES, and UV-vis spectroscopy, high-resolution mass spectrometry, magnetic moment measurements, and supporting CASSCF calculations.
Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 2056 - 2060 (2019/03/13)
The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.
