Iron mediated nitrenoid transfer: [(η5-C5H5)Fe(CO)2(THF)]+[BF4]− catalyzed aziridination of olefins

Heuss, Bruce D; Mayer, M.; Dennis, Shaun; Hossain, M. Mahmun

doi:10.1016/s0020-1693(02)01145-3

Cited by 44 publications

(19 citation statements)

References 25 publications

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“…The cationic complexes of type, [CpFe(CO) 2 L] + (L = labile ligand) [1][2][3][4] are an important class of transition metal compounds that have been extensively utilized in synthesis [2,[4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and catalysis [3,14,[22][23][24][25][26][27][28][29][30][31][32][33]. A particular example is the ethereal complex, [CpFe-(CO) 2 (THF)]BF 4 [34] in which the labile tetrahydrofuran (THF) is coordinated to the metal centre through the oxygen atom.…”

Section: Introductionmentioning

confidence: 99%

“…A particular example is the ethereal complex, [CpFe-(CO) 2 (THF)]BF 4 [34] in which the labile tetrahydrofuran (THF) is coordinated to the metal centre through the oxygen atom. This complex has been proven to be an essential precursor in the synthesis of various cyclopentadienyliron complexes [4,[10][11][12][13][15][16][17][18][19][20]35], as well as catalysts in various organic syntheses such as the [2+2] cycloaddition of alkenes [36], Diels-Alder reactions [37,38], cyclopropanation [27,[31][32][33], epoxidation [29,30] and aziridination [25][26][27][28], among others [3,[22][23][24]27,29,39]. In all these reactions THF is easily displaced by the desired substrate to form either the desired intermediate or desired end product.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

M’thiruaine

Friedrich

Changamu

et al. 2011

Inorganica Chimica Acta

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[{CpFe(CO) 2 } 2 l-(NH 2 (CH 2 ) n NH 2 )](BF 4 ) 2 (n = 2-4) (3), respectively. These complexes have been fully characterized and the mass spectral patterns of complexes 2 are reported. The structures of compounds 2a (n = 2) and 2b (n = 3) have been confirmed by single crystal X-ray crystallography. The single crystal X-ray diffraction data show that complex 2a, [CpFe(CO) 2 NH 2 (CH 2 ) 2 CH 3 ]BF 4 , crystallizes in a triclinic P 1 space group while 2b, [CpFe(CO) 2 NH 2 (CH 2 ) 3 CH 3 ]BF 4 , crystallizes in an orthorhombic Pca2 1 space group with two crystallographically independent molecular cations in the asymmetric unit. Furthermore, the reaction of 1 with 1-alkenes gives the g 2 -alkene complexes in high yield.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

M’thiruaine

Friedrich

Changamu

et al. 2011

Inorganica Chimica Acta

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“…Compared with porphyrin compounds, phthalocyanines are much easier to access and more stable to degradation. Iron phthalocyanine complex 4 (Scheme 10) used as catalyst for the aziridination of alkenes and PhINTs was reported by Zhou and co-workers [27]  5 also proved to be an efficient catalyst for the aziridination of styrene derivatives with PhINTs, as reported by Hossain and co-workers [28], affording the corresponding product with up to 85% yield (Scheme 11). Notablely, stereospecific products were obtained when internal alkenes were employed: cis-and trans-aziridines from cis-and trans-alkenes, respectively.…”

Section: Methodsmentioning

confidence: 83%

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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“…In 2003, Hossain and co-workers reported an additional successful application of [(η 5 -C 5 H 5 )Fe(II)(CO) 2 (THF)] + [BF4] − complex (which already showed catalytic activity in Diels-Alder reactions) to aziridination via imines and diazo compounds, cyclopropanation and epoxidation reactions. 86 The relatively mild iron Lewis acid was also found to be efficient in non-enantioselective aziridination of olefins using PhINTs (1 equiv.) as nitrene source.…”

Section: Iron-catalyzed Aziridination Of Terminal Alkenesmentioning

confidence: 99%

Non-heme iron catalysts for epoxidation and aziridination reactions of challenging terminal alkenes: towards sustainability

2015

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Iron mediated nitrenoid transfer: [(η5-C5H5)Fe(CO)2(THF)]+[BF4]− catalyzed aziridination of olefins

Cited by 44 publications

References 25 publications

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

Synthesis and characterization of amine complexes of the cyclopentadienyliron dicarbonyl complex cation, [Cp(CO)2Fe]+

Recent advances in the iron-catalyzed cycloaddition reactions

Non-heme iron catalysts for epoxidation and aziridination reactions of challenging terminal alkenes: towards sustainability

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