81090-31-5Relevant academic research and scientific papers
Preparation method for arylvinylsilane compound
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Paragraph 0074, (2020/02/14)
The invention relates to the technical field of chemical synthesis and discloses a preparation method for an arylvinylsilane compound. The preparation method comprises the following steps: adding a raw material A, a raw material B, a catalytic precursor and an oxidant into a reaction medium, and conducting reacting at 25-80 DEG C for 1-24 h; and then conducting separating to obtain the arylvinylsilane compound, wherein the raw material A is an aromatic hydrocarbon compound containing a heteroatom orienting group, the raw material B is vinylsilane and the catalytic precursor is a palladium salt. According to the preparation method, the vinylsilane and the aromatic hydrocarbon compound containing the heteroatom orienting group are used as the raw materials, the palladium salt is used as thecatalytic precursor and the oxidants including silver acetate and the like are added; then the components are subjected to a one-step reaction in an organic solvent to synthesize a target product. Themethod provided by the invention has the advantages of relatively good adaptability to substrates containing substituent groups having different properties, high yield, good stereoselectivity, no need of ligands, no need of protection of inert gas and simplicity in operation.
N -Methylation of ortho -substituted aromatic amines with methanol catalyzed by 2-arylbenzo [d] oxazole NHC-Ir(iii) complexes
Huang, Shuang,Hong, Xi,Cui, He-Zhen,Zhou, Quan,Lin, Yue-Jian,Hou, Xiu-Feng
, p. 5072 - 5082 (2019/04/17)
Seven new chelated cyclometalated Ir complexes of ABON,P, ABON,O, and ABON,C(carbene) based on a rigid and tunable 2-arylbenzo[d]oxazole backbone have been prepared for the N-methylation of amines. Among these three coordinated modes, ABON,C(carbene)-chelated iridium-based catalysts exhibited good performance in the monomethylation of aromatic amines with methanol (MeOH) as the green methylation reagent. The steric-modified synthesis of ABON,C(carbene) complexes was described. The most active ABON,C(carbene) complex with marginal steric hindrance as a catalyst was obtained from the benzoxazole ring without a substituent and methyl group of the benzimidazole ring on the N-heterocyclic carbene (NHC) ligand. A variety of amines including para- and meta-substituted aromatic amines, as well as heterocyclic amines, were formulated as suitable substrates. Importantly, this catalyst considerably promoted the yield of the N-methylation of ortho-substituted aromatic amines. Controlled kinetic experiments and deuterium-labeling reactions of these ortho-substituted amines were conducted under optimized conditions. On the basis of the experimental results, a plausible mechanism was proposed.
Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
supporting information, p. 2246 - 2252 (2017/03/17)
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
Intramolecular Pd-catalyzed anomeric C(sp3)-H activation of glycosyl carboxamides
Probst, Nicolas,Grelier, Gwendal,Ghermani, NourEddine,Gandon, Vincent,Alami, Mouad,Messaoudi, Samir
supporting information, p. 5038 - 5041 (2017/11/06)
An expedient method for the synthesis of fused glycosylquinolin-2-ones and glycosylspirooxindoles through an unprecedented intramolecular Pd-catalyzed anomeric C-H activation of the sugar moiety of 2-bromophenyl glycosylcarboxamides is reported. The scope of the reaction is broad and tolerates a wide range of functional groups.
Palladium-catalyzed α-arylation of enones in the synthesis of 2-alkenylindoles and carbazoles
Kale, Ajit Prabhakar,Kumar, Gangam Srikanth,Mangadan, Arun Raj Kizhakkayil,Kapur, Manmohan
, p. 1324 - 1327 (2015/03/14)
A new unified strategy has been developed for the synthesis of substituted 2-alkenylindoles and carbazoles. The strategy uses palladium-catalyzed α-arylation of TES-enol ethers of enones as the key step. The method is highly regioselective, provides good yields, and is expected to have wide application.
Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: Formal synthesis of the antilipemic drug fluvastatin
Kale, Ajit Prabhakar,Kumar, Gangam Srikanth,Kapur, Manmohan
, p. 10995 - 11002 (2015/11/25)
A new approach has been developed for the synthesis of substituted 2-alkenyl-3-arylindoles. The strategy comprises palladium-catalyzed dual α-arylation of TES-enol ethers of enones as the key step. This methodology results in products with very good yields and the regioselectivity is exclusive. We have also successfully used this dual α-arylation methodology in the formal synthesis of the cholesterol-lowering drug fluvastatin.
Syntheses of 2-unsubstituted 1h-1,3-benzazaphospholes from n-formyl-2-bromoanilides
Ghalib, Mohammed,Niaz, Basit,Jones, Peter G.,Heinicke, Joachim W.
, p. 452 - 459 (2013/12/04)
The phosphonylation of 2-bromo-formylanilides 1 with triethyl phosphite in the presence of preformed Pd(0)(triethyl phosphite)n catalyst furnished 2-phosphono-formanilides 2 in good yields. Reduction with excess LiAlH4 provided mainl
Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups
Hellwinkel, Dieter,Laemmerzahl, Frank,Hofmann, Gunter
, p. 3375 - 3405 (2007/10/02)
According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.
