Iron-Catalyzed [2π + 2π] Cycloaddition of α,ω-Dienes:  The Importance of Redox-Active Supporting Ligands

Bouwkamp, Marco W.; Bowman, Amanda C.; Lobkovsky, Emil; Chirik, Paul J.

doi:10.1021/ja064711u

Cited by 326 publications

(272 citation statements)

References 23 publications

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“…Significant improvement in iron-catalyzed [2 + 2] cycloaddition was achieved in 2006 by Chirik and co-workers (5). They reported an intramolecular [2 + 2] cycloaddition of the dienes resulting in the formation of [0.2.3] heptane derivatives catalyzed by a bis(imino)-pyridine iron(II) bis(dinitrogen) complex and only cis product was obtained.…”

Section: The [2 + 2] Cycloadditionmentioning

confidence: 99%

“…Products from both HySi and DHySi were generated depending on the substrate and reaction condition. In 1977, Schroeder and Wrighton (244c) disclosed a photoreaction of R 3 SiH and alkenes involving the same catalyst, Fe(CO) 5 . Later, they proposed a mechanism of iron-catalyzed HySi for the Cp*Fe(CO) 2 R catalytic system (Cp* = η 5 -C 5 Me 5 , R = alkyl, silyl) that included the insertion of a CC double bond into an Fe-Si bond.…”

Section: A Hydrosilylation Of Alkenesmentioning

confidence: 99%

See 1 more Smart Citation

Iron Catalysis in Synthetic Chemistry

Rana

Modak

Maity

et al. 2014

Progress in Inorganic Chemistry: Volume 59

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Section: The [2 + 2] Cycloadditionmentioning

confidence: 99%

Section: A Hydrosilylation Of Alkenesmentioning

confidence: 99%

Iron Catalysis in Synthetic Chemistry

Rana

Modak

Maity

et al. 2014

Progress in Inorganic Chemistry: Volume 59

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“…An iron-catalyzed intramolecular [2+2] cycloaddition of ,-dienes was reported by Chirik and co-workers [43]. In the presence of an iron bis(nitrogen) complex bearing a bis-(imino)pyridine ligand, ( iPr PDI)Fe(N 2 ) 2 (16-(N 2 ) 2 ), the cycloaddition of unactivated 1,6-heptadienes to [0.2.3]bicycloheptane afforded only the cis products with more than 90% conversion (Scheme 21).…”

Section: Scheme 20mentioning

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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“…Polymerisation [26] and increment values for hydrocarbon substituents. [24] The product was precipitated using 20 mL of MeOH, filtered and dried under vacuum at 50 8C for 5 h. Yield: 500 mg (99%).…”

Section: Polymer Synthesismentioning

confidence: 99%

Addition Polymers of Strained Cyclic Olefins – Transition Metal Catalysed Polymerisations of the Cyclobutene Derivative Bicyclo[3.2.0]hept‐6‐ene

Curran

Risse

Boggioni

et al. 2008

Macro Chemistry & Physics

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Bicyclo[3.2.0]hept‐6‐ene was converted into the corresponding addition polymer poly(6,7‐bicyclo[3.2.0]heptylene) with the aid of early and late transition metal based olefin polymerisation catalysts. Moderate to very good yields (42–99%) of polymer were obtained with [Pd(NCEt)4][BF4]2, [(η3‐allyl)Pd(solv)2][SbF6], [(2,9‐dimethyl‐1,10‐phenanthroline)Pd(CH3)(NC(CH2)6CH3)][SbF6], and Cp2ZrCl2/MAO, using monomer to transition metal ratios between 50/1 and 250/1. Reaction occurs at the olefin π‐bond, and the four‐membered ring of the monomer is retained during polymerisation which differs from ring‐opening olefin metathesis polymerisation in which the four‐membered ring is opened. The nearly exclusively saturated structure of the polymer was confirmed by 1H and 13C NMR spectroscopy. It is proposed that the polymers consist of repeating units that are predominantly cis‐exo‐enchained. GPC analysis of the soluble polymers prepared with [Pd(NCEt)4][BF4]2 showed that the molecular mass values $\overline M _{\rm n}$(GPC) were in the range of 3 700 to 22 600.magnified image

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Iron-Catalyzed [2π + 2π] Cycloaddition of α,ω-Dienes: The Importance of Redox-Active Supporting Ligands

Cited by 326 publications

References 23 publications

Iron Catalysis in Synthetic Chemistry

Iron Catalysis in Synthetic Chemistry

Recent advances in the iron-catalyzed cycloaddition reactions

Addition Polymers of Strained Cyclic Olefins – Transition Metal Catalysed Polymerisations of the Cyclobutene Derivative Bicyclo[3.2.0]hept‐6‐ene

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