137595-22-3Relevant academic research and scientific papers
Iridium-Catalyzed Isomerization of N-Sulfonyl Aziridines to Allyl Amines
Cabré, Albert,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier,Lledós, Agustí,Riera, Antoni
, p. 5747 - 5751 (2018)
The Crabtree's reagent catalyzes the isomerization of N-sulfonyl 2,2-disubstituted aziridines to allyl amines. The selectivity of allyl amine vs imine is very high (up to 99/1). The unprecedented isomerization takes place in mild conditions without activation of the catalyst by hydrogen. The mechanism has been studied computationally by DFT calculations; instead of the usual hydrogenation of COD, the catalytic species is formed by a loss of the pyridine ligand. Approaching of aziridine to this unsaturated species leads to a carbocation intermediate through a low energy barrier. A metal-mediated tautomerization involving sequentially γ-H elimination and N-H reductive elimination affords selectively the allyl amine. The readiness of the CγH bond to participate in the H elimination step accounts for the selectivity toward the allyl amine product.
Catalytic amination reactions mediated by Co(II) Schiff base complexes
Caselli, Alessandro,Gallo, Emma,Ragaini, Fabio,Oppezzo, Alessandro,Cenini, Sergio
, p. 2142 - 2148 (2005)
Co(acacen), 1, (acacen = 2,11-dihydroxy-4,9-dimethyl-5,8-diaza-2,4,8,10- dodecatetraene dianion) was found to be a highly efficient catalyst for the allylic amination of non activated alkenes, using N-(p-toluensulfonyl) iminophenyliodinane (PhINTs) as nitrene precursor. This reactivity has been extended to the less reactive C-H bond of toluene. The effect of reaction times and of added cosolvent on yields and selectivities was investigated. Under the best conditions, allylic amines were obtained in a 40-70% isolated yield. A complex derived from the stoichiometric reaction of Co(acacen), 1, with PhINTs has been isolated and spectroscopically characterized. Such a complex, although not able to transfer its NTs moiety to alkenes, is still active in catalyzing allylic amination of cyclohexene.
Catalytic asymmetric heterogeneous aziridination of alkenes using zeolite CuHY with [N-(p-tolylsulfonyl)imino]phenyliodinane as nitrene donor
Langham, Christopher,Taylor, Sophia,Bethell, Donald,McMorn, Paul,Bulman Page, Philip C.,Willock, David J.,Sly, Chris,Hancock, Frederick E.,King, Frank,Hutchings, Graham J.
, p. 1043 - 1049 (1999)
Copper-exchanged zeolite Y (CuHY) is found to be a highly effective heterogeneous catalyst for the aziridination of alkenes using [N-(p-tolylsulfonyl)imino]phenyliodinane (PhI=NTs) as the nitrogen source. Exchange of zeolite Y with other cations (Ag+
Catalytic heterogeneous aziridination of alkenes using microporous materials
Langham, Christopher,Piaggio, Paola,Bethell, Donald,Lee, Darren F.,McMorn, Paul,Bulman Page, Philip C.,Willock, David J.,Sly, Chris,Hancock, Frederick E.,King, Frank,Hutchings, Graham J.
, p. 1601 - 1602 (1998)
Copper-exchanged zeolite Y is a highly active catalyst for the aziridination of alkenes; modification using bis(oxazo-lines) leads to preparation of the first heterogeneous enantioselective aziridination catalyst.
Iron(III) porphyrin catalyzed aziridination of alkenes with bromamine-T as nitrene source
Vyas, Renu,Gao, Guang-Yao,Harden, Jeremiah D.,Zhang, X. Peter
, p. 1907 - 1910 (2004)
Equation presented. Iron(III) porphyrin complexes Fe(Por)Cl are effective catalysts for aziridination of alkenes using bromamine-T as the nitrene source. The catalytic system can operate under mild conditions with alkenes as limiting reagents. The aziridi
An efficient transition metal-free aziridination of alkenes with Chloramine-T using aqueous H2O2/HBr
Jain, Suman L.,Sharma, Vishal B.,Sain, Bir
, p. 8731 - 8732 (2004)
The combination of aqueous H2O2 and HBr was found to be an efficient transition metal-free green catalytic system for the aziridination of a variety of alkenes under very mild reaction conditions.
Practical aziridinations II: Electronic modifications to poly(pyrazolyl)borate-copper catalysts
Handy, Scott T.,Ivanow, Anatole,Czopp, Mark
, p. 1821 - 1823 (2006)
A significant influence of the electronic features of poly(pyrazolyl)borate ligands on the efficiency of the copper-catalyzed aziridination reaction has been noted. Electron-deficient, bidentate di(pyrazolyl)borates in conjunction with copper(II) chloride
Simple, Tunable Aziridination Catalysts Based on Poly(pyrazolyl)borate-Copper Complexes
Handy, Scott T.,Czopp, Mark
, p. 1423 - 1425 (2001)
matrix presented The in situ generation of a copper-poly(pyrazolyl)borate complex from copper chloride and a sodium poly(pyrazolyl)borate salt results in a catalyst that is effective for the aziridination of olefins. A significant influence of the combina
Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents
Kalra, Anshika,Bagchi, Vivek,Paraskevopoulou, Patrina,Das, Purak,Ai, Lin,Sanakis, Yiannis,Raptopoulos, Grigorios,Mohapatra, Sudip,Choudhury, Amitava,Sun, Zhicheng,Cundari, Thomas R.,Stavropoulos, Pericles
, p. 1974 - 1996 (2021/06/28)
Recent research has highlighted the key role played by the electron affinity of the active metal-nitrene/imido oxidant as the driving force in nitrene additions to olefins to afford valuable aziridines. The present work showcases a library of Co(II) reage
HKUST-1 Metal Organic Framework as an Efficient Dual-Function Catalyst: Aziridination and One-Pot Ring-Opening Transformation for Formation of β-Aryl Sulfonamides with C-C, C-N, C-S, and C-O Bonds
Sharma, Debesh,Rasaily, Sagarmani,Pradhan, Sajan,Baruah, Khanindram,Tamang, Sudarsan,Pariyar, Anand
supporting information, p. 7794 - 7802 (2021/05/26)
Metal-organic frameworks (MOFs) are extensively used in catalysis due to their robust structure, well-defined periodic reaction centers, and high porosity. We report Cu3(BTC)2·(H2O)3 (HKUST-1) as an efficient heterogeneous catalyst for aziridination of al
