Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst

Cramer, S. Alan; Jenkins, David M.

doi:10.1021/ja2090965

Cited by 198 publications

(195 citation statements)

References 41 publications

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“…1). For instance, exposure of a macrocyclic tetracarbene-ligated Fe-complex exclusively catalyzes the aziridination of aliphatic olens, 19 while a phthalocyaninato Fe-complex facilitates preferential intramolecular allylic C-H amination, allylic amine products.…”

Section: Introductionmentioning

confidence: 99%

Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

et al. 2014

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Section: Introductionmentioning

confidence: 99%

Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

et al. 2014

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“…M. Jenkins and co-authors [75,76] Interestingly, complex 154, when treated with para-substituted styrenes, was involved in aziridine cross-metathesis reactions yielding aziridino complexes 164-166 as well as styrene free (Scheme 27).…”

Section: Metal Carbene Catalystsmentioning

confidence: 99%

Aziridination of alkenes promoted by iron or ruthenium complexes

Damiano

Intrieri

Gallo

2018

Inorganica Chimica Acta

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Molecules containing an aziridine functional group are a versatile class of organic synthons due to the presence of a strained three member, which can be easily involved in ring-opening reactions and the aziridine functionality often show interesting pharmaceutical and/or biological behaviours. For these reasons, the scientific community is constantl y interested in developing efficient procedures to introduce an aziridine moiety into organic skeletons and the one-pot reaction of an alkene double bond with a nitrene [NR] source is a powerful synthetic strategy.Herein we describe the catalytic activity of iron or ruthenium complexes in promoting the reaction stated above by stressing the potential and limits of each synthetic protocol.

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“…More recently, Jenkins and co-workers [39] reported a tetracarbene iron(II) complex 12 catalyzed aziridination of aryl azides and a variety of substituted aliphatic alkenes (Scheme 17). Both electron-donating and -withdrawing aryl azides reacted effectively.…”

Section: Scheme 16mentioning

confidence: 99%

Recent advances in the iron-catalyzed cycloaddition reactions

Wang

Wan

2012

Chin. Sci. Bull.

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The rapid generation of molecular in a relatively easy manner has made the cycloaddition reaction a powerful tool in the synthesis of different membered ring compounds. Clearly, iron catalysts are becoming a much more interesting and viable choice for this purpose. In this review, a number of promising results in the iron catalyzed cycloaddition reactions in the last decades were summarized. Special attention has been paid to the asymmetric cycloaddition reactions. cycloaddition, iron catalyst, asymmetric Citation:Wang C X, Wan B S. Recent advances in the iron-catalyzed cycloaddition reactions. Chin Sci Bull, 2012, 57: 23382351, doi: 10.1007/s11434-012-5141-z Cycloaddition reaction, which can construct several bonds simultaneously in a single step, is one of the most powerful strategies for the synthesis of cyclic compounds from various unsaturated substrates such as alkynes, alkenes, allenes, nitriles, aldehydes, ketones, imines, etc. Three-, four-, five-, six-or seven-membered rings are obtained through these transformations. The high atom-efficiency, as well as the good tolerance of different functional groups, continues to draw many chemists' attention to this field. In particular, great efforts have been devoted to the development of novel and efficient catalytic systems. However, harsh reaction conditions are often required including heat, light, high pressure or sonication, and the lack of chemo-and/or regioselectivity is also an important problem. Over the past decades, the use of transition metal catalysts has contributed significantly to the development of the cycloaddition reactions and good selectivities were obtained [1]. Among all the available transition metals, iron is generally regarded as one of the most inexpensive, abundant, benign and relatively non-toxic metals [2]. Many transformations have been effectively promoted by iron catalysts, and excellent reviews on the iron-catalyzed reactions are available [3][4][5][6][7][8][9][10][11][12][13][14][15]. Bolm and co-workers [3] summarized the most important transformations with the aid of iron catalysts in 2004, including addition, substitution, cycloaddition, reduction and other reactions. At a later time, they also reviewed the oxidative C-C coupling reactions [4] and the development of carbon-heteroatom and heteroatom-heteroatom bond formation under iron catalysts [5]. The uses of FeCl 3 as catalyst in organic synthesis were covered by Padrón [6] and Bolm [4], and the cross coupling reactions were discussed in detail by Fürstner [7,8]. Recently, direct C-H transformation via iron catalysis was summarized by Shi and co-workers [9]. Applications of iron catalysts on other reactions were also summarized by Bauer [10] However, despite the aforementioned contributions, reviews mainly focus on the iron-catalyzed cycloaddition reactions are rather rare [15]. In this review, we will point out recent advances in this field, most contributions going from 2004 to Nov. 2011. Although every effort has been made to avoid repetition, some overlap with the ...

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Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst

Cited by 198 publications

References 41 publications

Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

Aziridination of alkenes promoted by iron or ruthenium complexes

Recent advances in the iron-catalyzed cycloaddition reactions

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