100-62-9Relevant articles and documents
Synthesis of imines from nitrobenzene and TiO2 particles suspended in alcohols via semiconductor photocatalysis type B
Rios-Bern?, Omar,Flores, Sergio O.,Córdova, Iván,Valenzuela, Miguel A.
, p. 2730 - 2733 (2010)
UV irradiation on a non-aqueous suspension of titanium dioxide with nitrobenzene and different alcohols in deaerated conditions produces imines and aniline as main products. The conversion of nitrobenzene and the corresponding selectivity of imines or aniline depend on the type of alcohol used. A low conversion (3-12%) and selectivity close to 100% to imines were obtained with methyl, ethyl, or propyl alcohol. Otherwise, using i-propanol only aniline was detected with a conversion of 13%. Finally, a mixture of aniline and imines was formed employing n-butyl, n-amyl, and i-amyl alcohols with the higher conversion (～50%).
Cyclocondensation of lower aliphatic aldehydes with arylamines and cyclopentadiene
Tolstikov,Savchenko,Lukina,Afon'Kina,Nedopekin,Khalilov,Odinokov
, (2013)
Three-component condensation of lower aliphatic aldehydes (C 1-C3) with arylamines and cyclopentadiene (the Povarov reaction) gave 3a,4,5,9b-tetrahydro-3H-cyclopenta[c]-quinolines. Ozonization of their N-trifluoroacetyl derivatives a
Carbonylation of nitrobenzene in methanol with palladium bidentate phosphane complexes: An unexpectedly complex network of catalytic reactions, centred around a Pd-imido intermediate
Mooibroek, Tiddo J.,Schoon, Lodi,Bouwman, Elisabeth,Drent, Eite
, p. 13318 - 13333 (2011)
The reactivity of palladium complexes of bidentate diaryl phosphane ligands (P2) was studied in the reaction of nitrobenzene with CO in methanol. Careful analysis of the reaction mixtures revealed that, besides the frequently reported reduction products of nitrobenzene [methyl phenyl carbamate (MPC), N,N′-diphenylurea (DPU), aniline, azobenzene (Azo) and azoxybenzene (Azoxy)], large quantities of oxidation products of methanol were co-produced (dimethyl carbonate (DMC), dimethyl oxalate (DMO), methyl formate (MF), H 2O, and CO). From these observations, it is concluded that several catalytic processes operate simultaneously, and are coupled via common catalytic intermediates. Starting from a P2Pd0 compound formed in situ, oxidation to a palladium imido compound P2PdII=NPh, can be achieved by de-oxygenation of nitrobenzene 1) with two molecules of CO, 2) with two molecules of CO and the acidic protons of two methanol molecules, or 3) with all four hydrogen atoms of one methanol molecule. Reduction of P 2PdII=NPh to P2Pd0 makes the overall process catalytic, while at the same time forming Azo(xy), MPC, DPU and aniline. It is proposed that the Pd-imido species is the central key intermediate that can link together all reduction products of nitrobenzene and all oxidation products of methanol in one unified mechanistic scheme. The relative occurrence of the various catalytic processes is shown to be dependent on the characteristics of the catalysts, as imposed by the ligand structure.
[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO
Guo, Can-Cheng,Li, Hui,Liu, Qiang,Luo, Wei-Ping,Nie, Zhiwen,Su, Miao-Dong,Yang, Tonglin
, (2022/02/10)
A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.
Precise regulation of the selectivity of supported nano-Pd catalysts using polysiloxane coatings with tunable surface wettability
Wang, Hongli,Gao, Ziqian,Wang, Xinzhi,Wei, Ruiping,Zhang, Junping,Shi, Feng
supporting information, p. 8305 - 8308 (2019/07/16)
A facile method was developed for surface modification of supported nano-Pd catalysts with tailorable wettability. The obtained Pd/TiO2@POS catalytic materials could be used in the controllable synthesis of styrene and ethylbenzene obtained from hydrogenation of phenylacetylene and the selective synthesis of imine and N-methylanilines via a reductive amination reaction. The precise modification of the hydrophilicity/hydrophobicity of the catalyst surface is crucial to realize this targeted transformation.
