Intramolecular Aromatic Amination through Iron‐Mediated Nitrene Transfer

Jensen, Michael P.; Mehn, Mark P.; Que, Lawrence

doi:10.1002/ange.200351605

Cited by 25 publications

(10 citation statements)

References 32 publications

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“…Nitrene addition to olefins and insertion into aliphatic C À H bonds have been reported in many instances; [4,5] however, very few examples of arene amination are known so far. [6][7][8][9] In particular, Que et al [8] described the intramolecular aromatic amination of a phenyl-bearing ligand upon treatment of a ferrous complex with PhI=NTs (Ts = 4-methylphenylsulfonyl). It is worth noting that the yield of the amine transfer culminates at about 64 % owing to hydrolysis of the iron nitrene active species, giving the hydroxylated product.…”

mentioning

confidence: 99%

Multiple Aromatic Amination Mediated by a Diiron Complex

et al. 2008

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confidence: 99%

Multiple Aromatic Amination Mediated by a Diiron Complex

et al. 2008

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“…A wide range of methods have been developed to prepare nanoporous carbons, including chemical vapor deposition (CVD) [19], templating [20,21] and chemical or physical activation method [22]. Inorganic hard templates like zeolites and mesoporous silica [23,24] and Soft template method [25,26] have been utilized to prepare nanoporous carbon particles.…”

Section: Introductionmentioning

confidence: 99%

Effect of carbonization temperature on adsorption property of ZIF-8 derived nanoporous carbon for water treatment

Abbasi

Shamsaei

Leong

et al. 2016

Microporous and Mesoporous Materials

134

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Effect of carbonization temperature on adsorption property of ZIF-8 derived nanoporous carbon for water treatment, Microporous and Mesoporous Materials (2016), doi: 10.1016/j.micromeso.2016 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractThe heat treatment effect on the adsorption capabilities of nanoporous carbon particles derived from Zeolitic Imidazolate Framework-8 (ZIF-8) was investigated at 600, 1000 and 1200 C in this study. The results showed that heat treatment at 1000 C had a significant effect on the adsorption capacity of ZIF-8 (almost 10 times) for the removal of methylene blue (MB) dye from water. Nanoporous carbons were synthesized by direct carbonization of ZIF-8. SEM and TEM images showed that the carbon resulting from ZIF-8 carbonization at various temperatures retained the original structure and morphology of ZIF-8. The carbon nanoparticles carbonized at 1000 C exhibited outstanding adsorption capacities (186.3 mg/g) compared to nanoparticles carbonized at 600 C (49.5 mg/g) and 1200 C (36.7 mg/g) as wellas ZIF-8 (19.5 mg/g) due to the change in surface charge and pore size distribution. The surface functionalities of materials were also characterized by Raman Spectroscopy, N 2 M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT2 adsorption-desorption, FTIR and TGA. The surface charge of the carbon particles changed from positive (ZIF-8) to negative as a result of conversion to carbon confirmed by zeta potential of the samples. The ZIF-8 derived carbon nanoparticles were found to be efficient adsorbents for water treatment purposes due to the satisfactory adsorption properties such as high adsorption capacity and good wettability.

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“…The same spectroscopic features were observed in low‐temperature experiments (down to −80 °C) in propionitrile (Figure S2). The 611 nm absorption could be associated with an Fe IV NTs species since they have been reported to have a low‐intensity absorption near 650 nm 8. 9 We thus monitored the reaction by Mössbauer spectroscopy at −80 °C in the hope of trapping 3 .…”

Section: Methodsmentioning

confidence: 99%

A Diiron(III,IV) Imido Species Very Active in Nitrene‐Transfer Reactions

et al. 2014

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Metal-catalyzed nitrene transfer reactions arouse intense interest as clean and efficient procedures for amine synthesis. Efficient Rh-and Ru-based catalysts exist but Fe alternatives are actively pursued. However, reactive iron imido species can be very short-lived and getting evidence of their occurrence in efficient nitrene-transfer reactions is an important challenge. We recently reported that a diiron(III,II) complex is a very efficient nitrene-transfer catalyst to various substrates. We describe herein how, by combining desorption electrospray ionization mass spectrometry, quantitative chemical quench experiments, and DFT calculations, we obtained conclusive evidence for the occurrence of an {Fe III Fe IV = NTosyl} intermediate that is very active in H-abstraction and nitrene-transfer reactions. DFT calculations revealed a strong radical character of the tosyl nitrogen atom in very low-lying electronic configurations of the Fe IV ion which are likely to confer its high reactivity.

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Intramolecular Aromatic Amination through Iron‐Mediated Nitrene Transfer

Cited by 25 publications

References 32 publications

Multiple Aromatic Amination Mediated by a Diiron Complex

Multiple Aromatic Amination Mediated by a Diiron Complex

Effect of carbonization temperature on adsorption property of ZIF-8 derived nanoporous carbon for water treatment

A Diiron(III,IV) Imido Species Very Active in Nitrene‐Transfer Reactions

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