439667-97-7Relevant academic research and scientific papers
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
Merging Photoredox/Nickel Catalysis for Cross-Electrophile Coupling of Aziridines with Pyridin-1-ium Salts via Dearomatization
Xu, Chong-Hui,Li, Jin-Heng,Xiang, Jian-Nan,Deng, Wei
supporting information, p. 3696 - 3700 (2021/05/04)
Merging photoredox/nickel catalysis enabling the cross-electrophile coupling of aziridines with pyridin-1-ium salts involving dearomatization for the synthesis of β-(1,4-dihydropyridin-4-yl)-ethylamines, especially including bioactive motif-based analogue
Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources
Berhal, Farouk,Grimaud, Laurence,Kirby, Georgina,Prestat, Guillaume,Vitale, Maxime R.
, p. 9428 - 9432 (2021/12/09)
The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is
Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines
Karjee, Pallab,Sarkar, Tanumay,Kar, Subhradeep,Punniyamurthy, Tharmalingam
, p. 8261 - 8270 (2020/07/25)
Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.
Regiodivergent and Stereospecific Aziridine Opening by Copper-Catalyzed Addition of Silicon Grignard Reagents
Yi, Hong,Oestreich, Martin
supporting information, p. 6505 - 6507 (2019/04/30)
A stereospecific ring opening of various 2-aryl-substituted aziridines with silicon Grignard reagents under copper catalysis is reported. The regiochemical outcome is governed by the steric demand of the silicon nucleophile. The LiCl introduced with the m
Stereospecific Ring Opening and Cycloisomerization of Aziridines with Propargylamines: Synthesis of Functionalized Piperazines and Tetrahydropyrazines
Das, Bijay Ketan,Pradhan, Sourav,Punniyamurthy, Tharmalingam
supporting information, p. 4444 - 4448 (2018/08/07)
Stereospecific Cu-catalyzed nucleophilic ring opening of N-sulfonylaziridines with propargylamines and subsequent hydroamination afford piperazines, which leads to double-bond isomerization to furnish tetrahydropyrazines. Optically active aziridines can be cross-coupled with high enantiomeric purities (>98% ee).
Correction to: Nickel-catalyzed enantioselective reductive cross-coupling of styrenyl aziridines (Journal of the American Chemical Society (2017) 139 (5688-5691) DOI: 10.1021/jacs.7b03448)
Woods, Brian P.,Orlandi, Manuel,Huang, Chung-Yang Dennis,Sigman, Matthew S.,Doyle, Abigail G.
supporting information, p. 7744 - 7745 (2018/06/26)
Table of Contents. The enantiomer of the BiOx ligand that delivers the indicated absolute configuration of product is (R,R)-(4-heptyl)BiOx. The corrected graphic is shown below: Page 5690. The absolute configuration of ligand L7 (4-heptyl- BiOx) was misas
Synthesis of indolines: Via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides
Liu, Ce,Liang, Yujie,Zheng, Nian,Zhang, Bo-Sheng,Feng, Yuan,Bi, Siwei,Liang, Yong-Min
supporting information, p. 3407 - 3410 (2018/04/05)
A Pd- and norbornene-catalyzed domino procedure has been developed to synthesize indoline compounds. This reaction provides efficient access to indolines by employing aryl iodides with aziridines as new electrophiles. The transformation is scalable and tolerates a range of functional groups.
Nickel(II)-Catalyzed [8 + 3]-Cycloaddition of 2-Aryl- N-tosylaziridines with Tropone
Liu, Honglei,Jia, Hao,Shi, Wangyu,Wang, Chang,Zhang, Cheng,Guo, Hongchao
supporting information, p. 3570 - 3573 (2018/06/26)
The Ni-catalyzed [8 + 3]-cycloaddition of tropone with 2-aryl-N-tosylaziridines proceeded smoothly under mild reaction conditions, affording various 4-tosyl-2,3,4,4a-tetrahydrocyclohepta[b][1,4]oxazine derivatives in moderate to excellent yields.
Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines
Sengoden, Mani,Bhowmick, Abhisikta,Punniyamurthy, Tharmalingam
supporting information, p. 158 - 161 (2017/11/27)
Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.
