Reaction of an Iron(IV) Nitrido Complex with Cyclohexadienes: Cycloaddition and Hydrogen-Atom Abstraction

Lee, Wei‐Tsung; Juarez, Ruth A.; Scepaniak, Jeremiah J.; Muñoz, Salvador B.; Dickie, Diane A.; Wang, Haobin; Smith, Jeremy M.

doi:10.1021/ic5010006

Cited by 52 publications

(49 citation statements)

References 57 publications

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“…The understanding of the structure of oxygen-transferring species can help to develop catalytic systems for oxidation reactions. Other examples are Fe N nitrido complexes that stoichiometrically transfer their nitrogen ligand to olefins [90]. [26,27] Iron Catalysis: Historic Overview and Current Trends 13 In 2009, Buchwald and Bolm published a paper where the issue of impurities in iron metal or salts and their influence on the course of a catalyzed reaction was addressed [91].…”

Section: Enantioselective Iron Catalysis and Stoichiometric Consideramentioning

confidence: 99%

Iron Catalysis: Historic Overview and Current Trends

Bauer

2015

Topics in Organometallic Chemistry

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Iron catalysis is a growing area of research, as seen by an exponential increase in the publication activities on the topic. This introductory chapter provides a historic overview of the development of iron catalysis including some notable milestones. The advantages of iron, i.e., its abundance, low price, and relative nontoxicity, are discussed, and an overview of the main type of reactions catalyzed by iron is outlined. The advances of heterogeneous iron catalysis (which is not covered in this volume) are exemplified with a few notable cases. Finally, the potential impact of metal impurities in iron sources on the catalytic activity is discussed.

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Section: Enantioselective Iron Catalysis and Stoichiometric Consideramentioning

confidence: 99%

Iron Catalysis: Historic Overview and Current Trends

Bauer

2015

Topics in Organometallic Chemistry

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“…13 Polydentate NHC ligands were found to stabilize high-valent iron species, which appeared to act as intermediates in catalytic oxidations and aziridations. [14][15][16][17][18][19][20] Only few examples for tetra-NHC ligand motifs are known to date. They exhibit either macrocyclic or acyclic structures.…”

Section: Introductionmentioning

confidence: 99%

Structural diversity of late transition metal complexes with flexible tetra-NHC ligands

et al. 2015

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The synthesis of copper, gold, nickel, palladium, platinum, and iron complexes with open chain tetra-N-heterocyclic carbene (NHC) ligands via transmetalation using silver NHC complexes is presented. The obtained complexes show differing coordination geometries depending on both ligand structure and metal. While the complexes of the coinage metals form di- or tetranuclear structures, the group 10 metal complexes exhibit a distorted square planar coordination geometry at the metal centers. In the case of iron an enhanced flexibility of the ligand - caused by a longer alkyl bridge - leads to octahedral complexes with a sawhorse-type coordination by the tetracarbene ligand and two cis acetonitrile ligands. To the best of our knowledge, this is the first known example of a tetracarbene ligand in sawhorse-type coordination within an octahedral coordination sphere. The remaining cis-labile sites are prone to exchange reactions as shown by addition of trimethylphosphine.

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“…1), [10],[11] are able to access diverse reaction pathways. Thus, we have chronicled two electron nitrogen atom transfer reactions to substrates such as C≡O, C≡NR and PR 3 , [10],[11a],[12],[13] one electron reactions with hydrogen atom donors and organic radicals, [11b],[14] and cycloadditions with conjugated dienes. [14] …”

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Styrene Aziridination by Iron(IV) Nitrides

et al. 2015

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Thermolysis of the iron(IV) nitride complex PhB(tBuIm)3Fe≡N with styrene leads to formation of the high spin iron(II) aziridino complex PhB(tBuIm)3Fe-N(CH2CHPh). Similar aziridination occurs with both electron-rich and electron-poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex PhB(tBuIm)3Fe-N(CH2CHPh) acts as a nitride synthon, reacting with electron poor styrenes to generate their corresponding aziridino complexes, i.e. aziridine cross-metathesis. Reaction of PhB(tBuIm)3Fe-N(CH2CHPh) with Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh) while simultaneously generating PhB(tBuIm)3FeCl. This closes a synthetic cycle for styrene azirdination by a nitride complex. While the less hindered iron(IV) nitride complex PhB(MesIm)3Fe≡N reacts with styrenes below room temperature, only bulky styrenes lead to tractable aziridino products.

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Reaction of an Iron(IV) Nitrido Complex with Cyclohexadienes: Cycloaddition and Hydrogen-Atom Abstraction

Cited by 52 publications

References 57 publications

Iron Catalysis: Historic Overview and Current Trends

Iron Catalysis: Historic Overview and Current Trends

Structural diversity of late transition metal complexes with flexible tetra-NHC ligands

Styrene Aziridination by Iron(IV) Nitrides

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