24955-07-5Relevant academic research and scientific papers
Palladium-catalyzed desulfitative heck-type reaction of aryl sulfinic acids with alkenes
Wang, Guan-Wu,Miao, Tao
, p. 5787 - 5790 (2011)
An efficient protocol has been developed for the desulfitative Heck-type reaction of aryl sulfinic acids with a variety of alkenes in the presence of a catalytic amount of Pd(OAc)2 and inexpensive Cu(OAc)2 as oxidant. This method does not require a ligand or a base, thereby broadening the scope of Pd-catalyzed coupling reactions. Copyright
Palladium-catalyzed decarboxylative coupling of α,β-unsaturated carboxylic acids with aryl tosylates
Zhang, Wei,Chen, Gairong,Wang, Kaikai,Xia, Ran
, (2019/04/27)
We report a general method for selective cross-coupling of α,β-unsaturated carboxylic acids with aryl tosylates enabled by versatile Pd(II) complexes. This method features the general cross-coupling of ubiquitous α,β-unsaturated carboxylic acids by decarboxylation. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Pd(II) catalysts, scalability and wide substrate scope. The reaction proceeds with high trans selectivity to furnish valuable (E)-1,2-diarylethenes.
Preparation method of palladium catalyzed 1,2-trans diaryl alkene
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Paragraph 0046-0048, (2019/06/11)
The invention discloses a preparation method of palladium catalyzed 1,2-trans diaryl alkene. The method comprises the following steps that under the effects of catalysts, cocatalysts and alkali, arylacrylic acid and aromatic esters p-toluene sulfonate take decarboxylation coupling reaction in an organic solvent; after the reaction is finished, the 1,2-trans diaryl alkene is obtained through posttreatment. The method has the advantages that through C-O bond fracture, the operation is simple; a stable palladium catalyst with low cost is used; the substrate applicability is high; the harsh reaction conditions and the addition of strong alkali are not needed; the trans 1,2-diaryl alkene can be generated at high selectivity.
Diarylethene synthesis method without transition metal catalysis
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Paragraph 0046-0050, (2019/02/06)
The invention discloses a diarylethene synthesis method without transition metal catalysis. The method comprises the following steps: a cinnamic acid derivative and aryl trifluoroborate are subjectedto a decarboxylation coupling reaction in a solvent under the action of an oxidizing agent, postprocessing is performed after the reaction, and diarylethene is obtained. K2S2O8 is adopted to promote acatalytic system in the synthetic method, and a free radical coupling reaction can be performed directly under the condition that no ligand, transition metal or alkali is added. The method has widersubstrate range and higher yield; the method is simple to operate, reaction conditions are mild, and large-scale application is facilitated.
Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group
Zhang, Na,Quan, Zheng-Jun,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
supporting information, p. 14234 - 14237 (2016/12/14)
The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.
Hydrogen Peroxide Promoted Mizoroki-Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes
Lasch, Roman,Fehler, Stefanie K.,Heinrich, Markus R.
supporting information, p. 1586 - 1589 (2016/05/02)
Mizoroki-Heck reactions, which are well-known for aryldiazonium salts and which have recently been described for arylhydrazines, have now been extended to phenyldiazenes. In situ generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium-silver(I) system.
Novel polymer supported iminopyridylphosphine palladium (∥) complexes: An efficient catalyst for Suzuki-Miyaura and Heck cross-coupling reactions
Liu, Xiang,Zhao, Xiaohua,Lu, Ming
, p. 23 - 27 (2014/07/21)
A novel cross-linked polyallylamine polymer supported iminopyridylphosphine palladium∥ complexes have been prepared and shown to be highly efficient catalysts for Suzuki-Miyaura and Heck cross-coupling reactions under low Pd loading (0.05% mol). Remarkably, the catalyst can be recycled and reused without loss of catalytic activity through simple filtration.
Design, synthesis and structure-activity relationships of some novel, highly potent anti-invasive (E)- and (Z)-stilbenes
Roman, Bart I.,De Coen, Laurens M.,Mortier, Séverine Thérèse F.C.,De Ryck, Tine,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
, p. 5054 - 5063 (2013/09/02)
In our ongoing exploration of the structure-activity landscape of anti-invasive chalcones, we have prepared and evaluated a number of structurally related (E)- and (Z)-stilbenes. These molecules exhibited an extraordinary high in vitro potency in the chick heart invasion assay, being active up to 10 nmol L-1, a concentration level a 100-fold lower than the lowest effective doses that have been reported for natural analogues. Furthermore, they possess an interesting pharmacological profile in silico.
Cu(acac)2-catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents and their olefination reaction with aromatic aldehydes
Fu, Ying,Hu, Xuemei,Chen, Yaojuan,Yang, Yanshou,Hou, Hongxia,Hu, Yulai
experimental part, p. 1030 - 1036 (2012/05/04)
An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields. Georg Thieme Verlag Stuttgart · New York.
Effects of substituent and solvent on the UV absorption energy of 4,4′-disubstituted stilbenes
Cao, Chenzhong,Chen, Guanfan,Wu, Yaxin
scheme or table, p. 1735 - 1744 (2012/05/05)
Twenty five samples of 4,4′-disubstituted stilbene derivatives were synthesized, and their UV absorption max wavelengths were determined in over 10 kinds of solvents including cyclohexane, ether, chloroform, acetonitrile and ethanol, in which 242 experimental data were recorded. The effects of substituents and solvents on the energy of their UV absorption max wavelengths were discussed. The research results showed: the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was mainly affected by their intramolecular structure (substituent effect) in a given solvent, that is, the energy is dominated by both of excited-state substituent parameter σ CC ex and polar substituent constant σ p. While their energy was dominated by the substituent effect and solvent effect in different kinds of solvents. An equation quantifying the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was developed. In addition, it is found that the n-octanol/water partition coefficient (logP) is more effective than the solvatochromic dye (E T(30)) in scaling the solvent effect. The equation employed the parameter logP has a better correlation and more specific physical meaning. Further, the energies of UV absorption max wavelengths of some reported compounds were predicted by the obtained equation, which are in agreement with their experimental values.
