129748-92-1Relevant academic research and scientific papers
Synthesis of Complexes with Protic NH,NR-NHC Ligands by Oxidative Addition of N-Alkyl-2-iodoimidazoles to [M(PPh3)4] (M = Pd, Pt) Complexes
Jin, Hanpeng,Kluth, Peter,Hahn, F. Ekkehardt
, p. 2774 - 2781 (2017)
The oxidative addition of N-methyl-2-iodoimidazole (1) or N-benzyl-2-iodoimidazole (2) to complexes [Pd(PPh3)4] or [Pt(PPh3)4] followed by the protonation of the unsubstituted imidazolato ring nitrogen atom yielded complexes trans-[M(NH,NMe-NHC)(PPh3)2I]PF6 (M = Pd: trans-[3]PF6; M = Pt: trans-[4]PF6) and trans-[M(NH,NBz-NHC)(PPh3)2I]PF6 (M = Pd: trans-[5]PF6; M = Pt: trans-[6]PF6) bearing imidazole-derived protic NH,NR-NHC (pNHC) ligands. In the absence of a proton source, the reaction of 1 with [Pd(PPh3)4] yielded the dinuclear dipalladium complex [7] featuring bridging imidazolato ligands metalated at the C2 ring-carbon atom and the N3 ring-nitrogen atom. Palladium complex trans-[3]PF6 undergoes halogen abstraction with AgPF6 to give acetonitrile complex trans-[Pd(NCCH3)(NH,NMe-NHC)(PPh3)2](PF6)2 trans-[8](PF6)2. This complex reacts further with 1,10-phenanthroline (phen), affording complex [Pd(NH,NMe-NHC)(PPh3)(phen)](PF6)2 [9](PF6)2.
Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination
Das, Ranajit,Banerjee, Mainak,Rai, Rakesh Kumar,Karri, Ramesh,Roy, Gouriprasanna
supporting information, p. 4243 - 4260 (2018/06/22)
The direct C2-H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2-H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2-H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C-H imination in a sequential one-pot reaction.
FRICTIONLESS MOLECULAR ROTARY MOTORS
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Page/Page column 31, (2010/02/17)
A rotaxane consisting of a cucurbituril and an uncharged guest molecule, having low or null affinity therebetween is provided as well as processes for providing the same. Various uses as energy converters (“frictionless” molecular motors), biochips and biosensors using the same are also provided.
Palladium-catalyzed intramolecular arylation of N-benzyl-2-iodoimidazoles: A facile and rapid access to 5H-imidazo[2,1-α]isoindoles
De Figueiredo, Renata Marcia,Thoret, Sylviane,Huet, Caroline,Dubois, Joelle
, p. 529 - 540 (2007/12/29)
The first example of a Pd-catalyzed intramolecular arylation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues. Georg Thieme Verlag Stuttgart.
Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH
Clyne, Mairead A.,Aldabbagh, Fawaz
, p. 268 - 277 (2007/10/03)
Six-membered photochemical cyclisations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. The decrease in yield of cyclisation products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclisation was only successful under photochemical conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinoline with nitric/sulfuric acid occurred at the 2- and 8-positions. The Royal Society of Chemistry 2006.
Lithiation of 1-Benzylimidazole. A Hypothesis on the Regioselectivity of the Electrophilic Attacks on the Lithiated Species
Moreno-Manas, M.,Bassa, J.,Llado, N.,Pleixats, R.
, p. 673 - 678 (2007/10/02)
Sequential lithiations of 1-benzylimidazole, 1, and of 1-benzyl-1,2,4-triazole,2, followed by treatment with electrophiles others than alkyl halides result in reactions at C-2.However, benzyl halides and, to a certain extent, iodomethane react at the N-benzyl carbon atom.An explanatory hypothesis based on steric ortho effects is advanced.
