A Micellar Iodide‐Catalyzed Synthesis of Unprotected Aziridines from Styrenes and Ammonia

Varszegi, Csaba; Ernst, Martin; Laar, Frederik van; Sels, Bert F.; Schwab, E.; Vos, Dirk De

doi:10.1002/anie.200704772

Cited by 46 publications

(20 citation statements)

References 40 publications

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“…The removal of these groups can sometimes be problematic because of the need for harsh reaction conditions. A direct aziridination method that would circumvent the need to use such a protecting group has so far remained elusive with few exceptions (6)(7)(8). Thus, practical and direct methods for the preparation of aziridines are very useful.…”

Section: A Simpler Route For Making Nitrogen-alkene Ringsmentioning

confidence: 99%

A Simpler Route for Making Nitrogen-Alkene Rings

Türkmen

Aggarwal

2014

Science

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Section: A Simpler Route For Making Nitrogen-alkene Ringsmentioning

confidence: 99%

A Simpler Route for Making Nitrogen-Alkene Rings

Türkmen

Aggarwal

2014

Science

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“…The use of micelles in the synthesis of aziridines from styrenes in a catalytic process is described by De Vos and co-workers. 13 The presence of non-ionic surfactants at concentrations above their cmc was found to ''boost'' the yield of aziridine in a process involving catalytic ''I + '' formed in situ through the oxidation of iodide by sodium hypochlorite. Ionic surfactants were not found to be effective in this process.…”

Section: Methodsmentioning

confidence: 99%

Reactivity in organised assemblies

Onel

Buurma

2009

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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This report reviews the 2008 literature on reactivity in organised assemblies. The report is subdivided in sections discussing (1) reactivity in micelles, including medium effects and compartmentalisation, enzymatic catalysis in micellar media and metallomicellar catalysis, (2) reactivity in vesicles, (3) reactivity in emulsions, (4) reactions in assemblies resulting from dynamic combinatorial chemistry and template approaches, (5) DNA-based approaches to influence reactivity including catalysis by DNA, DNA-templated synthesis and DNA-based asymmetric synthesis, (6) reactivity in nanoparticleimmobilised assemblies and (7) modulation of nanoparticle catalysis through the use of thermoresponsive polymers. We have chosen to interpret ''organised assemblies'' in a rather more liberal way than in previous years. [1][2][3] now including assemblies such as those involving DNA as well as constructions resulting from dynamic combinatorial self assembly which were turned into covalent ''non dynamic assemblies''. In all cases, however, (self) organisation and (self) assembly are crucial to the results discussed. Related to the liberal interpretation of organised assemblies, this report does not (and cannot) aim to present an exhaustive review.

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“…This method worked equally well with electron‐donating and electron‐withdrawing substituents. However, this method was found to be less efficient with aliphatic olefins …”

Section: Iodide‐catalyzed Synthesis Of Nh‐aziridines From Ammonia Andmentioning

confidence: 99%

Unprotected Aziridines: A Synthetic Overview

2017

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Unprotected (NÀH) aziridines are the key components in several biologically active natural products and important buildingb locks in organic synthesis. However,t he synthesis of unprotecteda ziridines is much more difficult than their oxygen counterparts (epoxides). Therefore, the development of efficient routes for their synthesis represents an attractive task fororganic chemists and, as aresult, avariety of methods have been developed. In this Focus Review, we have described the various approaches that have been reportedf or the synthesis of NH-aziridines.

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A Micellar Iodide‐Catalyzed Synthesis of Unprotected Aziridines from Styrenes and Ammonia

Abstract: Aziridines from ammonia: Unprotected aziridines are formed from styrenes in one catalytic step. Ammonia is incorporated directly using an aqueous micellar solution containing bleach as oxidant and sub‐stoichiometric amounts of iodide (see picture).

Cited by 46 publications

References 40 publications

A Simpler Route for Making Nitrogen-Alkene Rings

A Simpler Route for Making Nitrogen-Alkene Rings

Reactivity in organised assemblies

Unprotected Aziridines: A Synthetic Overview

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