Ring opening of aromatic heterocycles by uranium complexes

Duhović, Selma; Monreal, Marisa J.; Diaconescu, Paula L.

doi:10.1016/j.jorganchem.2010.08.003

Cited by 16 publications

(15 citation statements)

References 38 publications

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“…51 Compound 21 is an active precatalyst for both intra-and intermolecular alkyne hydroamination 54 and mediates aromatic heterocycle activation with a variety of substrates. [55][56][57][58] Both 21 and 23 can be made by in situ reaction of UI 3 (THF) 4 with 3 equivalents of benzyl potassium, presumably generating U(CH 2 Ph) 3 (THF) x , followed by 0.75 equivalent of fc(HNSiRMe 2 ) 2 in toluene and diethyl ether at −78 °C. 59 Variation of the alkylating reagent is possible, thus fc(NSi t BuMe 2 ) 2 -U(CH 2 SiMe 3 ) 2 (25) and fc(NSi t BuMe 2 ) 2 U(CH 2 CMe 3 ) 2 (26) have also been isolated.…”

Section: Non-cp Systemsmentioning

confidence: 99%

Achievements in uranium alkyl chemistry: celebrating sixty years of synthetic pursuits

Johnson

Bart

2015

Dalton Trans.

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Organouranium complexes containing uranium-carbon σ-bonds have been highly sought after since the initial exploration of these complexes during the 1950s. Since this time, a variety of uranium starting materials have been developed and alkylating reagents used in order to generate such species. Trivalent uranium alkyl compounds have recently moved past using the bis(trimethylsilyl)methyl ligand with the use of larger ancillary hydrotris(pyrazolyl)borate ligands. The uranium(iv) congeners are dominated by cyclopentadienyl ligands, but recent developments have shown that amides, alkoxides, and phosphines are also suitable ligand frameworks for supporting such species. A family of uranium(iv) alkyls formed via cyclometallation and neutral homoleptics have also been described. Highly reactive uranium(v) and (vi) alkyl complexes have recently been synthesized at low temperatures. The representative studies highlighted herein have helped to pioneer the field of organouranium alkyl chemistry.

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Section: Non-cp Systemsmentioning

confidence: 99%

Achievements in uranium alkyl chemistry: celebrating sixty years of synthetic pursuits

Johnson

Bart

2015

Dalton Trans.

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“…[14][15][16] Our group has studied extensively the reactivity of group 3 metals and uranium alkyl complexes supported by diamide ligands towards heterocyclic aromatic compounds. [17][18] Benzyl complexes were found to ring open 1-methylimidazoles, [19][20][21][22][23] effect C-C coupling of pyridines, [24][25] and alkyl transfer to isoquinoline. [26][27] In those cases, the ligand framework was a ferrocenediamide that could support a weak donor-acceptor interaction between the metal in the ligand.…”

Section: Introductionmentioning

confidence: 99%

Yttrium-Alkyl Complexes Supported by a Ferrocene-Based Phosphinimine Ligand

Brosmer

Diaconescu

2015

Organometallics

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The synthesis and characterization of two yttrium alkyl complexes supported by a bisphosphinimine ferrocene ligand, NP by NMR spectroscopy, electrochemical measurements, and elemental analysis. Reactivity studies were also carried out, however, the lack of prolonged thermal stability at ambient temperature of these molecules led to decomposition before the clean formation of reaction products could be observed.1

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“…[17][18][19] For uranium, we have observed a wide range of reactivity between tetravalent uranium complexes supported by such ligands and heterocycles. [20][21][22][23] For example, (NN TBS )U(CH2Ph)2 (NN TBS = fc(NSi t BuMe2)2, fc = 1,1'-ferrocenediyl) was found to mediate the double C-H activation, C-C coupling, alkyl transfer, and ring opening of aromatic N-heterocycles (Scheme 1). Some of these reactions were identified as separate steps, others as part of cascades.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Electronic Structure of Mono(1,1′-Diamidoferrocene) Uranium(IV) Complexes

et al. 2013

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The electronic structure of several mono(1,1'diamidoferrocene) uranium complexes (NN R)UX2 (NN R = fc(NR)2, fc = 1,1'-ferrocenediyl, R = SiMe3, Si t BuMe2, SiMe2Ph, X = I, CH2Ph), (NN TBS)UI(OAr) (OAr = 2,6-di-tertbutylphenoxide), and (NN TBS)U(CH2Ph)(OAr) was investigated by electrochemistry, electronic absorption and vibrational spectroscopy, and DFT calculations. Similar metrical parameters were observed for (NN TBS)U(CH2Ph)2 and (NN DMP)U(CH2Ph)2 (and also for the previously reported (NN TMS)UI2(THF), (NN TBS)UI2(THF), and (NN TBS)U(CH2Ph)(OAr)) that translate in similar DFT parameters (bond orders, metal charges) despite some small differences observed by electrochemistry and IR or electronic absorption spectroscopy.

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Ring opening of aromatic heterocycles by uranium complexes

Cited by 16 publications

References 38 publications

Achievements in uranium alkyl chemistry: celebrating sixty years of synthetic pursuits

Achievements in uranium alkyl chemistry: celebrating sixty years of synthetic pursuits

Yttrium-Alkyl Complexes Supported by a Ferrocene-Based Phosphinimine Ligand

Investigation of the Electronic Structure of Mono(1,1′-Diamidoferrocene) Uranium(IV) Complexes

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