NBS‐Mediated Aziridination between Styrenes and Amides under Transition Metal‐Free Conditions

Meng, Xu; Chen, Wenlin; Zhang, Yuanqing; Chen, Yongxin; Chen, Baohua

doi:10.1002/jhet.1555

Cited by 6 publications

(3 citation statements)

References 52 publications

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“…The use of 10 mol % iodine is sufficient to promote the transformation in the forward direction for completion . A catalyst-free aziridination process has also been reported. , We have used N , N -dibromo- p -toluenesulfonamide for the aziridination of various types of olefins in the presence of a base without any catalyst . The reaction was performed by treating the olefin with 1.2 equiv of olefin in the presence of 2.5 equiv of potassium carbonate (Scheme ).…”

Section: Aziridination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Aziridination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…14 In 2014, we reported a synthesis of aziridines by the aziridination of olefins and carboxamides in the presence of one equivalent of N-bromosuccinimide in CHCl 3 (Scheme 1). 15…”

Section: Synthesis Of Aziridinesmentioning

confidence: 99%

Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization

Liu

Huang

Meng

et al. 2019

Synlett

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The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.1 Introduction2 Synthesis of Aziridines3 Synthesis of Indoles and Indolizines4 Synthesis of Triazoles5 Synthesis of Imidazoles6 Synthesis of Oxazoles and Thiazoles7 Synthesis of Quinoxalines, Triazines, and Pyridines8 Conclusion and Outlook

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“…As a consequence, this has prompted a significant amount of effort toward the development of a myriad of synthetic methods to efficiently and selectively prepare the three-membered nitrogencontaining heterocycle. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] As part of an ongoing program exploring the reaction chemistry of iminoiodanes, we recently reported a facile synthetic approach to ,diacylaziridines involving Cu(II)-catalyzed aziridination of 2alkyl-substituted 1,3-dicarbonyl compounds with p-TsN=IPh (Scheme 1a). [38] Building on this initial work, we queried whether the construction of the aziridine motif in this manner could be achieved in the analogous reactions under transition metal-free mediated conditions (Scheme 1b).…”

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confidence: 99%

Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

et al. 2017

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The synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under Brønsted base-mediated atmospheric conditions is described. The reaction mechanism is thought to involve the formal oxidation of the substrate followed by aziridination of the ensuing α,β-unsaturated intermediate by the hypervalent iodine(iii) reagent.

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NBS‐Mediated Aziridination between Styrenes and Amides under Transition Metal‐Free Conditions

Cited by 6 publications

References 52 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization

Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

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