98251-31-1Relevant academic research and scientific papers
Pd-Catalyzed Cyclization of Alkynyl Norbornene Derivatives for the Synthesis of Benzofused Heteroarenes
Kwak, Hayeon,Kang, Eunsu,Song, Jae Yeong,Kang, Geunhee,Joo, Jung Min
, p. 4883 - 4888 (2021/09/09)
Modular approaches, which allow a systematic variation of heteroaromatic cores and substituents, are crucial for the development of heteroaromatic drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The precursors were readily prepared by a three-component coupling process of heteroaryl halides, norbornadiene, and terminal alkynes. The Pd catalytic system derived from Pd(OAc)2 and 2-(pyrazol-1-yl)pyridine transformed a variety of five-membered heteroarenes to the corresponding benzofused products, including (di)benzothiophene, indazole, carbazole, indole, and benzofuran, with aryl and alkyl substituents at the C4(C7) position. During the cyclization process, the norbornene ring underwent a retro-Diels-Alder reaction, serving as an acetylene synthon. This approach was used to synthesize naphthalene derivatives from electron-rich arenes, demonstrating its versatility in the annulation of (hetero)aromatic rings. (Figure presented.).
COMPOUND, MATERIAL FOR AN ORGANIC ELECTROLUMINESCENCE DEVICE AND AN ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE COMPOUND
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Paragraph 0237; 0251, (2021/08/20)
Specific compounds represented by formula (I), a material for an organic electroluminescence device comprising said specific compound, an organic electroluminescence device comprising said specific compound, an electronic equipment comprising said organic
Suzuki-Miyaura Cross-Coupling of Sulfoxides
Abduhulam, Hayrul,Cao, Changsheng,Chen, Qianwei,Dang, Yanfeng,Li, Chengxi,Shi, Yanhui,Wu, Shufeng,Yan, Shuqin
, p. 8168 - 8176 (2020/09/18)
The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the Suzuki-Miyaura reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reactions showed good functional group compatibility, proceeded well under mild conditions, and provided biaryls in yields of up to 96%. A wide range of useful functional groups, such as fluoro, chloro, ether, hydroxyl, amide, cyano, keto, trimethylsilyl (TMS), and ester were tolerated under the reaction conditions; however, the use of phenylboronic anhydride and arylboronic acid pinacol esters generally would lead low yields. Good regioselectivity for the electron-poor phenyl group was achieved when unsymmetrical diphenyl sulfoxides were used. The protocol is applicable at the gram scale even with half the amount of catalyst. Density functional theory calculations were performed to investigate the reaction mechanism, indicating that the reaction occurred through oxidative addition, transmetalation, and reductive elimination to provide the final coupling product.
Organic compound and organic electroluminescent device
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Paragraph 0120; 0121; 0122-0124, (2020/04/02)
The present invention relates to the field of organic electroluminescence, and can provide an organic compound represented by a general formula (1). The present invention also provides an organic electroluminescent element produced by using the compound as a hole transport material.
Compound, application thereof and organic light-emitting device comprising compound
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Paragraph 0050; 0055-0057, (2021/01/04)
The invention relates to a compound, application thereof and an organic light-emitting device comprising the compound. The compound has a structure as shown in the following formula (1), wherein X isselected from O, S or Se; L1 is selected from substitute
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0174-0178, (2020/07/28)
The present invention provides a compound represented by chemical formula 1 and an organic light emitting device comprising the same. The organic light emitting device according to the present invention has excellent lifespan characteristics and high luminous efficiency even at a low driving voltage.COPYRIGHT KIPO 2020
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0251-0255, (2020/07/29)
The present invention provides a compound of chemical formula 1 and an organic light emitting device comprising the same. The organic light emitting device containing the compound has excellent lifespan characteristics and can have high luminous efficiency even at a low driving voltage.COPYRIGHT KIPO 2020
Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons: Via palladium catalysis
Liu, Chengwei,Qin, Zhi-Xin,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
, p. 5736 - 5742 (2019/06/18)
Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding via well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism. The utility of this reaction is highlighted in the direct defunctionalization of pharmaceuticals and natural products, and further emphasized in a range of traceless processes using removable carboxylic acids under mild, redox-neutral conditions orthogonal to protodecarboxylation. Extensive DFT computations were conducted to demonstrate preferred selectivity for the reversible oxidative addition and indicated that a versatile hydrogen atom transfer (HAT) pathway is operable.
N, C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions
Thakore, Ruchita R.,Takale, Balaram S.,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
, p. 11647 - 11657 (2019/11/29)
Various monosubstitution and disubstitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied while looking for ways to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that (1) preactivation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with approximately half the loading of Pd, relative to that previously required based on a combination of a Pd(II) salt and ligand; and (3) the most effective palladacycle precatalyst has been identified as that containing an isopropyl group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion (P13). This precatalyst is also effective in other C-C bond-forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A one-pot, four-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this precatalyst to maximize synthetic gain while minimizing costs and waste generation.
Transition-Metal-Free Cross-Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)-1,3-Dienes
?iau?iulis, Mindaugas,Ahlsten, Nanna,Pulis, Alexander P.,Procter, David J.
supporting information, p. 8779 - 8783 (2019/06/19)
A transition metal-free one-pot stereoselective approach to substituted (E,Z)-1,3-dienes was developed by using an interrupted Pummerer reaction/ligand-coupling strategy. Readily available benzothiophene S-oxides, which can be conveniently prepared by oxidation of the parent benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)-1,3-dienes.
