21711-00-2Relevant articles and documents
Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
supporting information, p. 9995 - 9998 (2021/10/06)
The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.
Direct Synthesis of N,N-Disubstituted Formamides by Oxidation of Imines Using an HFIP/UHP System
Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro
, p. 11072 - 11079 (2020/10/12)
The straightforward synthesis of N,N-disubstituted formamides using a combination of 1,1,1,3,3,3-hexafluoroispropanol (HFIP) and H2O2 is described. The unique features of HFIP allowed the utilization of a green oxidant such as H2O2, and the products, arising from an oxidation-rearrangement sequence, were obtained in good to high yields under smooth reaction conditions.
Atom economical synthesis of: N -alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant
Kra?em, Jamil,Ollevier, Thierry
supporting information, p. 1263 - 1267 (2017/08/15)
A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.
Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights
Ghosh, Asit,Mandal, Subhajit,Chattaraj, Pratim Kumar,Banerjee, Prabal
supporting information, p. 4940 - 4943 (2016/10/18)
A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.
Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines
Kivrak, Arif,Larock, Richard C.
supporting information; experimental part, p. 7381 - 7387 (2011/02/22)
Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes.
[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants
Jain, Suman L.,Singhal, Sweety,Sain, Bir
, p. 2930 - 2935 (2008/02/02)
Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.
An environmentally friendly oxidation system for the selective oxygenation of aldimines to oxaziridines with anhydrous TBHP and alumina-supported MoO 3 as a recyclable heterogeneous catalyst
Singhal, Sweety,Jain, Suman L.,Prasad,Sain, Bir
, p. 2051 - 2054 (2008/02/04)
A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported M0O3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Iron and manganese (III) - Porphyrins as new applicable catalysts for selective oxidation of imines with urea-hydrogen peroxide
Karami, Bahador,Montazerozohori, Morteza,Moghadam, Majid,Farahi, Mahnaz
, p. 275 - 277 (2008/02/09)
A variety of imines were oxidised with urea-hydrogen peroxide using iron(III) and manganese (III)- tetraphenylporphyrins [Fe(TPP)Cl], [Mn(TPP)Cl] and manganese (III)-octabromotetraphenyl porphyrin [Mn(TPPBr8)Cl] as catalysts. Experimental resul
An inexpensive and selective oxygenation of N-alkyl imines to oxaziridines
Shailaja,Manjula,Rao, B. Vittal
, p. 1176 - 1178 (2007/10/03)
A range of N-alkyl imines was oxidised to corresponding oxaziridines in a highly selective manner with sodium tungstate-30% H2O2 in acetonitrile under mild conditions.
Stereospecific synthesis of 2-alkyl-3-aryloxaziridines from prochiral and chiral N-arylidenealkylamines by use of the benzonitrile-hydrogen peroxide system
Kraiem,Kacem,Khiari,Ben Hassine
, p. 263 - 271 (2007/10/03)
Benzonitrile-hydrogen peroxide oxidation of prochiral and chiral imines 1a-h leads to racemic (E)-oxaziridines (R,R/S,S) and nonracemic (E)-oxaziridines (R,R,R/S,S,R) 2a-h, respectively.
