Iron‐Catalyzed Aziridination Reactions

Nakanishi, Masafumi; Salit, Anne-Frédérique; Bolm, Carsten

doi:10.1002/adsc.200700519

Cited by 124 publications

(53 citation statements)

References 82 publications

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“…was also reported by Bolm and co-workers [33] in the presence of a simple iron salt Fe(OTf) 2 (Scheme 14). The in situ generated iminoiodianes from the mixtures of the corresponding sulfonamide and PhI(OAc) 2 made this reaction a variation of the aforementioned aziridination of PhINTs with alkenes [34].…”

Section: Methodsmentioning

confidence: 57%

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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Section: Methodsmentioning

confidence: 57%

Recent advances in the iron-catalyzed cycloaddition reactions

Wang

Wan

2012

Chin. Sci. Bull.

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“…On the other hand, Che and co‐workers showed that alkene aziridination in the presence of [Fe(Cl 3 terpy) 2 ] 34 (Cl 3 terpy = 4,4′,4″‐tri‐ tert ‐butyl‐2,2′:6′2″‐terpyridine, Figure 2f) as catalyst was applicable to a wider range of starting alkenes and gave the corresponding products in 68–97% yield (Table 2, entry 12) 29. This work was followed by a report by Bolm and co‐workers, who demonstrated a Fe(OTf) 2 ‐catalyzed version of this reaction that gave the corresponding products in moderate to good yields of 24–90% (Table 2, entry 13) 30…”

Section: Intermolecular Aziridination Of Alkenes With Phintsmentioning

confidence: 86%

“…Bolm and co‐workers demonstrated that an iron(II)‐catalyzed version of this process could also be accomplished 30. When the substrates 53 were exposed to Fe(OTf) 2 and PhINTs, the corresponding α‐amino ketones 55 were attained in moderate to good yields of 46–72%.…”

Section: Intermolecular Aziridination Of Silyl Enol Ethersmentioning

confidence: 99%

Transition‐metal‐catalyzed aminations and aziridinations of CH and CC bonds with iminoiodinanes

Chang

Ton

Chan

2011

The Chemical Record

203

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Catalytic insertion or addition of a metal-imido/nitrene species, generated from reaction of a transition-metal catalyst with iminoiodanes, to C-H and C=C bonds offers a convenient and atom economical method for the synthesis of nitrogen-containing compounds. Following this groundbreaking discovery during the second half of the last century, the field has received an immense amount of attention with a myriad of impressive metal-mediated methods for the synthesis of amines and aziridines having been developed. This review will cover the significant progress made in improving the efficiency, versatility and stereocontrol of this important reaction. This will include the various iminoiodanes, their in situ formation, and metal catalysts that could be employed and new ligands, both chiral and non-chiral, which have been designed, as well as the application of this functional group transformation to natural product synthesis and the preparation of bioactive compounds of current therapeutic interest.

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“…The filtrate was removed under reduced pressure to obtain the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 10/1 as eluent) to yield corresponding product. The identity and purity of the products was confirmed by 1 H and 13 C NMR spectroscopic analysis.…”

Section: Methodsmentioning

confidence: 99%