Highly Efficient Alkene Epoxidation and Aziridination Catalyzed by Iron(II) Salt + 4,4′,4′′-Trichloro-2,2′:6′,2′′-terpyridine/4,4′′-Dichloro-4′-<i>O</i>-PEG-OCH<sub>3</sub>-2,2′:6′,2′′-terpyridine

Liu, Peng; Wong, Ella Lai‐Ming; Yuen, Angella Wing‐Hoi; Che, Chi‐Ming

doi:10.1021/ol801157m

Cited by 107 publications

(66 citation statements)

References 38 publications

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“…A highly robust and efficient catalyst for the epoxidation of olefins was introduced by Che and co‐workers,77 in which the homoleptic Fe II bisterpyridine complex [Fe( 3 a ) 2 ]Cl 2 in combination with potassium peroxomonophosphate (oxone), as oxidant, oxidized a wide range of alkene derivatives to the corresponding epoxides in high yields and diastereoselectivities. For instance, aryl alkenes (either terminal or internal) were oxidized almost quantitatively without formation of the 1,2‐diol in which the cis ‐stilbene was oxidized in 96 % yield and 96 % diastereoselectivity ( cis / trans ratio of 27:1).…”

Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

“… The epoxidation of an α,β‐unsaturated steroid catalyzed by a homoleptic Fe II bisterpyridine complex 77…”

Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

“…Liu et al. showed that both the aziridination of alkenes and amidation of sulfamate esters proceeded in high yields when this particular catalyst was used 77. Styrenes, as well as terminal and cyclic alkenes, were transformed into the corresponding N ‐substituted aziridines by reaction with a nitrene‐transfer reagent according to Scheme .…”

Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

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Catalytic Applications of Terpyridines and their Transition Metal Complexes

2011

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The coordination compounds of the tridentate oligopyridine ligand 2,2′:6′,2′′‐terpyridine (tpy) are utilized in very different fields of research, such as materials science (e.g. photovoltaics), biomedicinal chemistry (e.g. DNA intercalation), and organometallic catalysis. Applications in the latter area have arisen from initial reports on electro‐ or photochemical processes and, today, a broad range of reactions—from artificial photosynthesis (water splitting) to biochemical and organic transformations as well as polymerization reactions—have been catalyzed by terpyridines and their transition metal complexes. In this review, the scope and the limitations of these applications, which emerged particularly in organic and macromolecular chemistry, will be evaluated.

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Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

“… The epoxidation of an α,β‐unsaturated steroid catalyzed by a homoleptic Fe II bisterpyridine complex 77…”

Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

Section: Tri‐n‐oxides and Complexes Of 22′:6′2′′‐terpyridines As Camentioning

confidence: 99%

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Catalytic Applications of Terpyridines and their Transition Metal Complexes

2011

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“…Although iron complexes containing tetra-or pentadentate nitrogen ligands were not good catalysts for styrene aziridination with PhINTs [30], six-coordinated iron complex 11 (Scheme 13) resulting from two terpyridine ligands was an effective catalyst for intermolecular and intramolecular aziridination of alkenes [32]. The intermolecular aziridination of aromatic and aliphatic alkenes with PhINTs or PhINNs afforded the aziridine products in good yields.…”

Section: Methodsmentioning

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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“…These complexes perform well in alkene epoxidations (66-89% yield with 90-98% selectivity in 5 min at room temperature). Furthermore, recyclable terpyridines 5 lead to highly active Fe II -complexes, which show good to excellent results (up to 96% yield) for the epoxidation with oxone at room temperature (Scheme 4) [36]. Scheme 4 Selected ligands for iron-catalyzed epoxidation of alkenes…”

Section: Epoxidation Of Olefinsmentioning

confidence: 99%