29265-83-6Relevant academic research and scientific papers
Synthetic method of 1,1-diarylethenes derivative
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Paragraph 0146; 0148; 0151; 0154; 0157; 0158, (2018/10/11)
The invention discloses a synthetic method of a 1,1-diarylethenes derivative. The synthetic method comprises the following steps: with cinnamic acid derivatives and aryltriethoxysilane as raw materials, mixing the raw materials with a catalyst, an oxidizing agent, a ligand, an additive and alkali; carrying out reaction for 2 to 24 hours at 100 to 160 DEG C under argon protection in a reaction solvent so as to prepare a target compound. Because cinnamic acid is common unsaturated carboxylic acid, the preparation is convenient, cinnamic acid is cheap and easy to obtain; because aryltriethoxysilane is common organosilane in organic chemistry, aryltriethoxysilane is cheap and easy to obtain, is higher in stability and has little impact on an environment; therefore, the 1,1-diarylethenes derivative is synthesized by carrying out coupled reaction between the selected aryltriethoxysilane and the cinnamic acid derivatives. The synthetic method has the advantages of cheap and easy availabilityof the raw materials and low production cost; meanwhile, an experiment is easy to operate, and the synthetic method can be developed as an industrialized production method. According to the syntheticmethod disclosed by the invention, synthetic conditions are also screened and optimized, so that the reaction yield is further improved.
Pd-catalyzed cross-coupling reactions with carbonyls: Application in a very efficient synthesis of 4-aryltetrahydropyridines
Barluenga, Jose,Tomas-Gamasa, Maria,Moriel, Patricia,Aznar, Fernando,Valdes, Carlos
supporting information; experimental part, p. 4792 - 4795 (2009/05/07)
A method is proposed to prepare 4-aryltetrahydropyridines by a Pd-catalyzed cross-coupling reaction by using tosylhydrazone as the nucleophilic coupling agent without stoichiometric organometallic reagent. Palladium-catalyzed couplings can be used for the formation of C-C linkages. It was observed during study that tosylhydrazone can be generated by employing 4-piperidones directly in the cross-coupling reaction with tetrahydropyridines in very high yields. It was also found during study that the ketones and aldehydes can be employed as nucleophilic coupling partners in a reaction without using stoichiometric organometallic reagent. The study concluded that the method can be used to prepare different types of di- and trisubstituted olefins at large scale.
Decarbonylative Heck olefination of enol esters: Salt-free and environmentally friendly access to vinyl arenes
Goossen, Lukas J.,Paetzold, Jens
, p. 1095 - 1098 (2007/10/03)
Thank you, no salt on the side. In this variant of the Heck olefination, enol esters serve as environmentally friendly synthetic equivalents of aryl halides. These reactants, in turn, are available from a waste-free synthesis from carboxylic acids and propyne. Thus, a salt-free overall process has been devised for preparing vinyl arenes from a variety of aromatic carboxylic acids.
The effect of meta- or para-cyano substitution on the reactivity of the radical cations of arylalkenes and alkanes. Radical ions in photochemistry, Part 34
Arnold, Donald R.,Du, Xinyao,Chen, Jing
, p. 307 - 318 (2007/10/03)
The effect of electron-withdrawing substituents, meta- or para-cyano, on the reactivity of the radical cation of arylalkenes and alkanes has been determined.The radical cations were generated by single electron transfer (set) to an electron-accepting photosensitizer.Three reactions were studied: (i) the addition of nucleophile to the radical cation of arylalkanes, (ii) cleavage of the benzylic carbon-carbon bond of the radical cation of arylalkanes; and (iii) the deprotonation of the benzylic carbon-hydrogen bond of the radical cation of arylalkanes.The radical cations of 4-(1-phenylethenyl)benzonitrile (1b), 3-(1-phenylethenyl)benzonitrile (1c), 4-(2-methoxy-1-phenylethyl)benzonitrile (2b), 3-(2-methoxy-1-phenylethyl)benzonitrile (2c), cis- and trans-5-cyano-2-methoxy-1-phenylindane (6b-cis and -trans), and 6-cyano-3-phenylindene (7b) were generated, by single electron transfer to the lowest excited singlet state of 1,4-dicyanobenzene (3), in acetonitrile-methanol.The radical cations of 1b, 1c, and 7b react with methanol to yield the anti-Markovnikov adducts (2b, 2c, and 6b-cis and 6b-trans).The radical cations of 2b, 2c, and 6b-trans cleave at the benzylic carbon-carbon bond to give products derived from the radical and carbocation fragments.The radical cation of 6b-cis deprotonates from the benzylic position with subsequent formation of the diastereomer, 6b-trans.This behaviour can be explained/predicted on the basis of the proposed mechanisms for these reactions.Molecular orbital calculations (AM1) support the conclusions.Key words: photosensitized, electron transfer, radical ions, radicals, molecular orbital calculations (AM1).
