Iron(III) Porphyrin Catalyzed Aziridination of Alkenes with Bromamine-T as Nitrene Source

Vyas, Renu; Gao, Geng; Harden, Jeremiah D.; Zhang, X. Peter

doi:10.1021/ol049691k

Cited by 144 publications

(53 citation statements)

References 36 publications

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“…PhI=NR compounds leading N-substituted aziridines [27], several papers were published up to 2006 [28][29][30][31][32]. As stated above, the catalytic sustainability of iron complexes is currently pushing the scientific community to devote more attention to the study of the catalytic properties of these species.…”

Section: 1mentioning

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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Section: 1mentioning

confidence: 99%

Aziridination of alkenes promoted by iron or ruthenium complexes

Damiano

Intrieri

Gallo

2018

Inorganica Chimica Acta

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“…Gross and co-workers [36] disclosed an iron(III) corrole complex catalyzed aziridination of styrene derivatives with chloramines-T, whereas Zhang and co-workers [37] reported an aziridination of alkenes with bromamine-T in the presence of Fe(TPP)Cl (Scheme 15). Although only moderate yields were obtained in both cases, the main by-product NaCl and NaBr instead of PhI can be easily removed from the reaction system and thus allowing the procedure to be more practical.…”

Section: Scheme 13 Scheme 14mentioning

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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“…Bromamina-T (N-bromo-N-sodio-ptoluenossulfonamida ou TsNNaBr) tem se apresentado como melhor agente doador de nitreno em relação à Cloramina-T, na aziridinação de diferentes alquil e aril olefinas 85 sob catálise de CuCl ou metalo-porfirinas. Já a catálise por PdCl 2 se mostrou mais eficiente 86 para aziridinação de olefinas deficientes de elétrons, com rendimentos entre 20 e 81%.…”

Section: Azidasunclassified

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Bisol¹,

Sá²

2007

Quím. Nova

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Recebido em 22/8/05; aceito em 3/2/06; publicado na web em 30/8/06RECENT ADVANCES IN THE PREPARATION OF AZIRIDINES AND THEIR APPLICATION IN ORGANIC SYNTHESIS. This article surveys a selection of the most recent advances in aziridine synthesis. Novel synthetic methods and new insights into existing methodologies for the selective construction of the title compounds reported in the past decade are discussed in terms of synthetic applicability and environmentally benign conditions. Mechanisms involving stereoselective preparation of structurally diverse aziridines are also presented in order to highlight the most important issues associated with the synthesis of these versatile building blocks.

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Iron(III) Porphyrin Catalyzed Aziridination of Alkenes with Bromamine-T as Nitrene Source

Cited by 144 publications

References 36 publications

Aziridination of alkenes promoted by iron or ruthenium complexes

Aziridination of alkenes promoted by iron or ruthenium complexes

Recent advances in the iron-catalyzed cycloaddition reactions

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

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