27761-02-0Relevant articles and documents
Nickel dithiolenes containing pendant thiophene units: Precursors to dithiolene-polythiophene hybrid materials
Anjos, Tania,Roberts-Bleming, Susan J.,Charlton, Adam,Robertson, Neil,Mount, Andrew R.,Coles, Simon J.,Hursthouse, Michael B.,Kalaji, Maher,Murphy, Patrick J.
, p. 475 - 483 (2008)
The synthesis, electrochemical and spectroscopic properties of the new thiophene-substituted metal dithiolene complexes [Ni(b-3ted)2] (3) and [NBu4][Ni(b-3ted)2] ([NBu4][3]) are described [b-3ted = bis(3-thienyl)-1,2-ethylenedithiolene] and compared with new studies of the known compounds [Ni(b-2ted)2] (2) and [NBu 4][Ni(b-2ted)2] ([NBu4][2]). X-Ray structures were determined for the neutral complexes 2 and 3 and both showed planar nickel dithiolene units with thiophene groups twisted out of the molecular plane, precluding close molecular π-stacking. Electrochemical investigations revealed two redox processes corresponding to interconversion between neutral, monoanionic and dianionic species for 3, analogous to 2. Oxidation of 0.1 mM [3]- in CH3CN was shown to give a green molecular film of 3 which, in contrast to as-prepared crystals of 3, showed significant conductivity. Electrochemical polymerisation of 3 carried out at different concentrations resulted in films; electrochemical, SNIFTIRS and UV-Vis results were consistent with incorporation of the intact metal dithiolene complex in these films. In contrast, electrochemical polymerisation of 2 gave a film charateristic of a polymerised thiophene but with no evidence of incorporation of the intact metal dithiolene complex. Copolymerisation of 3 with thiophene gave a gold-coloured electropolymerised film of significant conductivity that, upon dissolution in CH2Cl2, showed the characteristic low energy absorption of the Ni-dithiolene complex, confirming its incorporation. This copolymerisation approach offers a versatile route to the synthesis of metal dithiolene-polythiophene hybrid films. The Royal Society of Chemistry.
A thiophene-derived hexaazatriphenylene (HAT) fluorescent sensor for the selective detection of Ag+ ion
Zhang, Xiang,Fan, Yu,Zhan, Tian-Guang,Qi, Qiao-Yan,Zhao, Xin
, (2021)
Herein, by symmetrically merging six thiophene units into the hexaazatriphenylene (HAT) core, a HAT-based sensor (1) was designed and synthesized, which was found capable of exhibiting selective recognition of Ag+ with detection limit as low as 1.79 × 10?6 M in chloroform featuring with significant fluorescence “turn-off” property. Through the systematical investigation with UV–Vis absorption, fluorescence spectroscopy and the naked-eye experiments, as well as the 1H NMR titration and the Job's plot, it was revealed that sensor 1 could complex with Ag+ in a stoichiometric ratio of 2:3. We envisage the construction of such a thiophene-derived HAT molecule is conducive to exploring new type of Ag+ sensors, and it also will bring potential application in environmental detection.
Synthesis of functionalized γ-lactones via a three-component cascade reaction catalyzed by consecutive N-heterocyclic carbene systems
Zhao, Qian,Han, Bo,Wang, Biao,Leng, Hai-Jun,Peng, Cheng,Huang, Wei
, p. 26972 - 26976 (2015/03/30)
Two consecutive N-heterocyclic carbene (NHC) catalytic systems were combined in a one-pot cascade reaction for the assembly of aromatic aldehydes and 2-haloenals into a structurally complex γ-lactone backbone. To our knowledge, this is the first report of NHC-catalyzed [3 + 2] annulation of α,β-unsaturated acylazoliums with 1,2-bisnucleophiles.
One-pot asymmetric synthesis of substituted tetrahydrofurans via a multicatalytic benzoin/Michael/acetalization cascade
He, Gu,Wu, Fengbo,Huang, Wei,Zhou, Rui,Ouyang, Liang,Han, Bo
supporting information, p. 2311 - 2319 (2014/07/21)
A sequential benzoin/Michael/acetalization tandem reaction catalyzed by NHC and amine together has been developed to assemble aromatic aldehydes and enals into chiral tetrahydrofuran derivatives bearing multiple functional groups and stereogenic centers with high stereoselectivity of up to 95:5 dr and 96% ee. The high yield and stereocontrol of this process may be due to both acid-promoted symmetrization of racemic acyloins and iminium ion activation of enals.
Enantioselective reduction and deracemisation using the non-conventional yeast Pichia glucozyma in water/organic solvent biphasic systems: Preparation of (S)-1,2-diaryl-2-hydroxyethanones (benzoins)
Fragnelli, Maria Caterina,Hoyos, Pilar,Romano, Diego,Gandolfi, Raffaela,Alcántara, Andrés R.,Molinari, Francesco
experimental part, p. 523 - 528 (2012/01/13)
Water/organic solvent two-liquid-phase systems have been successfully applied in the synthesis of enantiomerically pure (S)-benzoin through two different methodologies catalysed by whole cells from the non-conventional yeast Pichia glucozyma: the stereoselective monoreduction of benzil and the deracemisation of benzoin. The presence of the organic solvent influences the redox systems implied in the reactions, avoiding the formation of the corresponding diols, increasing the enantioselectivity and allowing the easy isolation of the products in high yields and excellent enantiomeric excesses. The use of both strategies has been extended to the preparation of different chiral benzoin derivatives.
One-pot synthesis of quinoxalines starting from aldehydes under metal-free conditions
Hu, Zhong-Yuan,Du, Ding,Tang, Wei-Fang,Lu, Tao
experimental part, p. 2262 - 2264 (2012/08/07)
An efficient and convenient synthesis of quinoxalines from easily available aldehydes was performed as a one-pot procedure in good to excellent yields under metal-free conditions, via sequential benzoin condensation, aerobic formation of benzils and condensation of the latter with 1,2-diaminobenzenes.
Study on the reactivity of aldehydes in electrolyzed ionic liquids: Benzoin condensation - Volatile organic compounds (VOCs) vs. room temperature ionic liquids (RTILs)
Chiarotto,Feroci,Orsini,Feeney,Inesi
supporting information; experimental part, p. 3287 - 3292 (2011/02/23)
The benzoin condensation of aromatic and heteroaromatic aldehydes, catalyzed by electrochemically generated N-heterocyclic carbenes, has been set up in the absence of organic solvents and bases. α-Hydroxy ketones have been isolated in good to elevated yields, in short reaction times. Aldol products and carbene-aldehyde adducts have been obtained in elevated yields from linear and short branched aldehydes, respectively. A comparison with the use of classical organic solvents has been reported Copyright
Methylene-bridged bis(benzimidazolium) salt as a highly efficient catalyst for the benzoin reaction in aqueous media
Iwamoto, Ken-Ichi,Kimura, Hitomi,Oike, Masaaki,Sato, Masayuki
experimental part, p. 912 - 915 (2008/10/09)
Benzoin reactions are catalyzed effectively by a methylene-bridged bis(benzimidazolium) salt to yield α-hydroxy ketones, and the reactions proceed in water as the aqueous medium under mild conditions. The Royal Society of Chemistry.
Benzoin reaction in water as an aqueous medium catalyzed by benzimidazolium salt
Iwamoto, Ken-ichi,Hamaya, Masako,Hashimoto, Naoki,Kimura, Hitomi,Suzuki, Yumiko,Sato, Masayuki
, p. 7175 - 7177 (2007/10/03)
Benzoin reactions are catalyzed by N,N-dialkylbenzimidazole to yield α-hydroxy ketones; the reaction proceeds in water as an aqueous medium under mild conditions. The utility of these salts as pre-catalysts in these reactions has been demonstrated.
Microwave assisted benzoin condensation using thiamine as catalyst
Bag, Seema,Vaze, Vidula V.,Degani, Mariam S.
, p. 267 - 269 (2007/10/03)
α-Hydroxyketones were prepared in appreciable yields at a very high speed, (by the benzoin condensation) under microwave irradiation using a catalytic amount of thiamine hydrochloride, from various aromatic as well as heteroaromatic aldehydes. They can be used as intermediates in NCE synthesis.
