137595-22-3Relevant articles and documents
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 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+
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
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
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
, 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
Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
, 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.
