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Carbonylation Reactions of a Metallapentalyne:Synthesis of Its Ester and Amide Derivatives
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作者 Yongfa Zhu Dafa Chen +1 位作者 Ming Luo Haiping Xia 《Chinese Journal of Chemistry》 SCIE CAS 2024年第22期2765-2772,共8页
omprehensive Summary Carbonylation reactions are a valuable synthetic method to construct carbonyl compounds and carbonylation reactions of aryl halides stand out as a highly significant tool for generating carbonyl s... omprehensive Summary Carbonylation reactions are a valuable synthetic method to construct carbonyl compounds and carbonylation reactions of aryl halides stand out as a highly significant tool for generating carbonyl substituted arenes.However,the important reactions have never been realized in aromatic metallacycles.Herein,we present the first carbonylation reactions of metallaaromatics,specifically alkoxycarbonylation and aminocarbonylation reactions of an osmapentalyne.During the carbonylation process,the electronic and steric properties of nucleophiles are regarded as critical factors.The alcohols with bulky substituents(isopropanol)require more reaction time and tert-butyl alcohol is inert in the reaction.Comparatively,amines,being stronger nucleophiles,exhibit divergent behaviors.Bulky amines undergo aminocarbonylation,whereas small amines prefer direct nucleophilic additions.Control experiments revealed that the intermediate derived from coupling of metal carbyne with CO plays a significant role in the carbonylation reaction.According to these observations,a divergent pathway for the reaction is proposed.Furthermore,the photophysical properties of these carbonyl-functionalized osmapentalene complexes are studied,and the maximum absorption peak of compound with a carboxylic group exhibits a significant red-shift due to the smaller HOMO-LUMO gap.These findings contribute to expanding the reactivity of metallaaromatics and offer new opportunities for the synthesis of carbonyl-functionalized metallacycles. 展开更多
关键词 carbonylation reactions Metal carbyne Aromaticity Carbon monoxide Metallacycle
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Development of palladium-catalyzed Suzuki carbonylation reaction without external ligand and its application in modification of novel series of α7 nAChR PAMs
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作者 Ying Meng Wenxing Zou +6 位作者 Zongze Huang Xintong Wang Wenxuan Jiao Wenjun Xie Xiling Bian KeWei Wang Qi Sun 《Journal of Chinese Pharmaceutical Sciences》 CAS CSCD 2018年第7期460-468,共9页
Palladium-catalyzed Suzuki carbonylation with CHCl3 as carbonylative reagent was realized without external ligands. Different substituted benzophenones were explored via the coupling reaction of aryl iodides, arylboro... Palladium-catalyzed Suzuki carbonylation with CHCl3 as carbonylative reagent was realized without external ligands. Different substituted benzophenones were explored via the coupling reaction of aryl iodides, arylboronic acids and CHCl3 as a CO surrogate in moderate to good yields. This method was also successfully applied to the structure modification of α7 nicotinic acetylcholine receptor positive allosteric modulators(α7 nAChR PAMs) based on the preliminary structure-activity relationship. 展开更多
关键词 carbonylation reaction Palladium-catalysis BENZOPHENONES CO surrogate
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Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction 被引量:1
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作者 杨妲 王栋梁 +4 位作者 刘欢 赵小莉 路勇 赖时军 刘晔 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2016年第3期405-411,共7页
The neutral palladium(Ⅱ) complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-imidazolyl]dichloropalladium(Ⅱ)(1A) ligated by thiazolylimidazolyl-based phosphine(L1) in which thiazolylimidazolyl acted as an... The neutral palladium(Ⅱ) complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-imidazolyl]dichloropalladium(Ⅱ)(1A) ligated by thiazolylimidazolyl-based phosphine(L1) in which thiazolylimidazolyl acted as an S- and N-donor provider with weak coordinating nature,and the ionic complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-3-methylimidazolium]dichloropalladium(Ⅱ) trifluoromethanesulfonate(2A) ligated by thiazolylimidazolium-based phosphine(L2) after quaternization of L1 using methyl trifluoromethanesulphonate were synthesized.It was found that the introduced positive charges and strong electron-withdrawing effect in 2A not only led to changes in the configuration and structural stability of the complex,but also lowered its catalytic performance in carbonylative Sonogashira reactions.These effects reveal the important role of the N-donor in 1A.In addition,as an ionic palladium complex,2A combined with the room-temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate could be recycled eight times as the catalyst in carbonylative Sonogashira reactions without detectable metal leaching. 展开更多
关键词 Ionic phosphine ligand Palladium complex Carbonylative Sonogashira reaction Ionic liquid
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Zeolite-Catalyzed Acetalization Ⅰ. Synthesis of Some Acetals and Ketals through Reaction of Carbonyl Compounds with Ethanediol 被引量:2
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作者 Wei JIANG Yan TIAN +1 位作者 Yu Dao MA Qi Long WANG(Department of Chemistry, Shandong University, Jinan 250100)Lei WANG(Department of Pharmacy, Shandong Medical University, Jinan, 250012) 《Chinese Chemical Letters》 SCIE CAS CSCD 1997年第5期377-380,共4页
The acetalization of a series of carbonyl compounds with ethanediolwas performed over two self-steaxned HY zeolle catalpsts' The acetal and ketaiproducts were obtained with high ytelds Espectw, the HY zeollte with... The acetalization of a series of carbonyl compounds with ethanediolwas performed over two self-steaxned HY zeolle catalpsts' The acetal and ketaiproducts were obtained with high ytelds Espectw, the HY zeollte with highfraxnework Si/A1 ratio was proven to be suitable cataipst for the acetabotion ofunsaturated carbonyl compounds, during which the C =C double bond was notperturbed 展开更多
关键词 Synthesis of Some Acetals and Ketals through reaction of Carbonyl Compounds with Ethanediol
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Optically Active β-Hydroxy Carbonyl Compound from a Mukaiyama Reaction Catalyzed by M-Salen Complex
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《厦门大学学报(自然科学版)》 CAS CSCD 北大核心 1999年第S1期227-227,共1页
关键词 Optically Active Hydroxy Carbonyl Compound from a Mukaiyama reaction Catalyzed by M-Salen Complex
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Palladium-catalyzed 3,4-hydroaminocarbonylation of conjugated dienes for formation ofβ,γ-unsaturated amides
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作者 Hui-Yi Yang Liang-Quan Lin +2 位作者 Na-Qi Li Zhi-Hui Ren Zheng-Hui Guan 《Science China Chemistry》 SCIE EI CAS CSCD 2023年第5期1474-1481,共8页
Hydrocarbonylation of conjugated dienes is one of the most promising yet challenging methods for the synthesis of carbonyl compounds.Herein,we reported the development of an unprecedented palladium-catalyzed branched ... Hydrocarbonylation of conjugated dienes is one of the most promising yet challenging methods for the synthesis of carbonyl compounds.Herein,we reported the development of an unprecedented palladium-catalyzed branched selective 3,4-hydroaminocarbonylation of 1,3-dienes with CO and amines hydrochloride to affordβ,γ-unsaturated amides.This reaction employs readily available starting materials(including anilines,amines,amino acids,peptides,aryl-1,3-dienes,alyl-1,3-dienes)and tolerates a wide range of functional groups,thus providing a facile and effective approach to access a diverse array ofα-substitutedβ,γ-unsaturated amides.Mechanistic investigations suggested that the hydropalladation of dienes is irreversible,and the insertion of CO into the allyl-Pd species is probably the rate-limiting step. 展开更多
关键词 PALLADIUM-CATALYZED carbonylation reaction regioselectivity conjugated diene amides synthesis
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Regioselective synthesis of linalyl compounds via addition reaction of geranyl bromide and tin with carbonyl compounds
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作者 ZHOU,Jing-Yao LU,Guo-Di CHEN,Zhao-Gen WU,Shi-Hui Department of Chemistry,Fudan University,Shanghai 200433 《Chinese Journal of Chemistry》 SCIE CAS CSCD 1993年第2期164-168,共8页
Linalyl alkyl or aryl carbinols were regioselectively synthesized by the reaction of geranyl bromide and powdered tin with aldehydes and ketones.
关键词 PPM HC Regioselective synthesis of linalyl compounds via addition reaction of geranyl bromide and tin with carbonyl compounds
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Facile synthesis of isoindoline-l,3-diones by palladium-catalyzed carbonylative cyclization of o-bromobenzoic acid and primary amines
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作者 Mayur V. KHEDKAR Bhalchandra M. BHANAGE 《Frontiers of Chemical Science and Engineering》 SCIE EI CAS CSCD 2013年第2期226-232,共7页
A facile method for the carbonylative cycliza- tion of o-bromobenzoic acid with primary amine using Pd(OAC)2 as a metal precursor and 1, l′-bis(diphenylpho- sphino)ferrocene (dppf) as a ligand has been develope... A facile method for the carbonylative cycliza- tion of o-bromobenzoic acid with primary amine using Pd(OAC)2 as a metal precursor and 1, l′-bis(diphenylpho- sphino)ferrocene (dppf) as a ligand has been developed. The effect of various reaction parameters such as ligand, solvent, base, time and temperature on this cyclization was studied. The optimized protocol was used for a wide variety of substituted aryl amines with different steric and electronic properties, affording the corresponding isoindoline-l,3-diones in good to excellent yields under atmospheric pressure of carbon monoxide at 100℃ within 10h using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base. The reaction system finds attractive alternative to the conventional multistep synthetic process and thus repre- sents an effective utilization of carbonylative protocol for synthesis of valuable chemicals. 展开更多
关键词 carbonylative cyclization reactions isoindole-1 3-dinones homogeneous catalysis DPPF
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