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palladium-catalyzed oxidative cyclopropanation of enamides and norbornenes initiated by C–H activation

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Science China Chemistry 2018年第6期61卷 695-701页

作者： Ming Chen Mi-Na Zhao Yao-Du Zhang Zhi-Hui Ren Zheng-Hui Guan Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education Department of Chemistry & Materials Science Northwest University Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences

A novel palladium-catalyzed oxidative cyclopropanation of enamides and norbornenes has been developed. The reaction proceeded through palladium-catalyzed vinyl C–H bond activation of enamides followed by two migratory insertions, β-(N)H elimination and hydrolyzation cascade steps. The reaction tolerates a range of functional groups and provides an effective method for the synthesis of cyclopropane-fused norbornanes in good yields under mild conditions.

关键词： palladium-catalyzed cyclopropanation C–H activation enamides norbornenes

palladium-catalyzed Three-Component Coupling Reaction of Allyl Carboxylates, Norbornenes and Diboronates InvoIving Sequential Olefins Insertion and Borylation Reaction

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Chinese Journal of Chemistry 2019年第2期37卷 140-147页

作者： Zun Li Jia Zheng Chunsheng Li Wanqing Wu Huanfeng Jiang Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong 510640China

Summary of main observation and conclusion An efficient Pd-catalyzed three-component coupling reaction of allyl carboxylates, norbornenes and diboronates is described, which allows efficient assembly of C(sp3)-C(sp3) and C(sp3)-B bonds in a single process. Moreover, this approach shows advantages of good chemo- and regioselectivity, as well as good substrates suitability.

关键词： palladium-catalyzed Three-Component Coupling Reaction Allyl Carboxylates

palladium-catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes

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Chinese Journal of Chemistry 2023年第2期41卷 181-187页

作者： Songjia Fang Huanfeng Jiang Wanqing Wu Key Laboratory of Functional Molecular Engineering of Guangdong Province State Key Laboratory of Luminescent Materials and DevicesSchool of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong 510640China

This report discloses a distinctive palladium-catalyzed sequential tandem cyclization reaction of two molecular haloalkynes and one molecular N-alkylanilines,leading to the efficient assembly of various 3-halo-1,2,5-triarylpyrrole *** carbon-carbon tri-ple bonds and one carbon-halogen bond in two molecular haloalkynes are transformed conveniently in one single step,which may involve the aminoalkynylation of haloalkyne and cyclization of the newly formed enyne *** high chemo-and regiose-lectivities,good functional group tolerance and late-stage modification of the halopyrrole products further illustrate the synthetic value of this strategy.

关键词： palladium-catalyzed Haloalkynes N-Alkylanilines Cyclization Halopyrroles Amines Insertion Synthetic methods

palladium-catalyzed Intermolecular Oxidative Diazidation of Alkenes

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Chinese Journal of Chemistry 2017年第6期35卷 876-880页

作者： Haihui Peng Zheliang Yuan Pinhong Chen Guosheng Liu State Key Laboratory of Organometallics Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

A palladium-catalyzed oxidative vicinal diazidation of alkenes has been developed, in which TMSN3 was used as azide source. Both styrenes and unactivated alkenes are suitable for this reaction. And trans-alkyldiazides were obtained as major products from cyclic alkenes with moderate to good diastereoselectivities. This reaction afforded an efficient way for the synthesis of useful 1,2-diamines after hydrogenation.

关键词： palladium-catalyzed azidation alkene styrene

palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring

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Chinese Chemical Letters 2021年第2期32卷 713-716页

作者： Xiai Luo Wenguang Li Haiyan Lu Guobo Deng Yuan Yang Chunming Yang Yun Liang National&Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources Key Laboratory of Chemical Biology and Traditional Chinese Medicine ResearchMinistry of EducationKey Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan ProvinceCollege of Chemistry and Chemical EngineeringHunan Normal UniversityChangsha 410081China Hunan University of Medicine Huaihua 418000China

A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladiumcatalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides,which provides an efficient method for synthesizing various aryl-substituted spirocyclic *** protocol enables three C-C bonds formation via an intramolecular Heck reaction and sequentially regioselective C-H bond activation.

关键词： palladium-catalyzed Cascade reaction Regioselective C-H activation Naphthalene ring Spirocyclic oxindoles

palladium-catalyzed oxidative homocoupling of 2-arylquinazolinones

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Chinese Chemical Letters 2020年第12期31卷 3263-3266页

作者： Yadong Feng Zhengping Wu Ting Chen Qi Fu Qihua You Jinhai Shen Xiuling Cui College of Einviranment and Public Health Xiamen Huaxia UniversityXiamen 361024China Research Center of Molecular Medicime Mdinistry of EducationKey Laboratory of Fujian Molecular MedicineKey laboratory of Precision Medicine and Molecular Dinghosis of Fujian UniversitiesKey Laboratory of Xiamen Marine and Cene DrugsSchool of Bionedical SciencsHuaqiao University Xiamen 361021China

Pd-catalyzed oxidative homocoupling of 2-arylquinazolinones was successfully developed for the direct construction of biaryls via C—H bond *** well-defined structure that possessed two quinazolinone units was obtained with high efficiency and atomic *** protocols offer an efficient approach to the synthetically useful and functionalized biaryls in good yields using quinazolinone as a directing group.

关键词： 2-Arylquinazolinones Homocoupling palladium-catalyzed C—H bond activation

palladium-catalyzed sulfonylative coupling of benzyl(allyl)carbonates with arylsulfonyl hydrazides

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Green Synthesis and Catalysis 2022年第1期3卷 110-115页

作者： Bozhen Gong Haibo Zhu Yishuai Liu Qian Li Liu Yang Guorong Wu Qiangwen Fan Zongbo Xie Zhanggao Le Jiangxi Province Key Laboratory of Synthetic Chemistry East China University of TechnologyNanchang 330013China Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices East China University of TechnologyNanchang 330013China

An efficient palladium-catalyzed sulfonylative coupling for the synthesis of benzyl(allyl)sulfones from sulfonyl hydrazides and carbonates was *** novel methodology employs easily accessible chemical feedstocks including stable and readily available arylsulfonyl hydrazides and benzyl(allyl)carbonates.A variety of benzyl(allyl)sulfones could be obtained in good to excellent yields in the presence of Pd(dppf)Cl2 without additional base under mild conditions.

关键词： Benzylic(allylic)sulfones Sulfonyl hydrazides Carbonates C-O cleavage palladium-catalyzed

palladium-catalyzed Asymmetric Domino Heck/Carbocyclization/Suzuki Reaction:A Dearomatization of Nonactivated Naphthalenes

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CCS Chemistry 2021年第12期3卷 69-77页

作者： Ming Chen Xucai Wang Zhi-Hui Ren Zheng-Hui Guan Key Laboratory of Synthetic and Nature Molecule of Ministry of Education Department of Chemistry and Materials ScienceNorthwest UniversityXi’an 710127

Herein,we report a novel palladium(Pd)-catalyzed asymmetric domino Heck/carbocyclization/Suzuki reaction of N-(2-bromoaryl)-*** reaction involves a novel and enantioselective dearomative 1,2-insertion of the naphthalene group,thus providing a unique dearomatization strategy of nonactivated naphthalenes.A new phosphoramidite ligand L12,which displayed excellent reactivity and enantioselectivity in the reaction,has been developed.

关键词： asymmetric catalysis palladium-catalyzed domino Heck reaction dearomatization nonactivated naphthalenes

Electrochemical palladium-catalyzed Intramolecular C-H Amination of 2-Amidobiaryls for Synthesis of Carbazoles

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Chinese Journal of Chemistry 2021年第1期39卷 143-148页

作者： Qingqing Wang Xiaojing Zhang Pan Wang Xinlong Gao Heng Zhang Aiwen Lei College of Chemistry and Molecular Sciences Institute for Advonced Studies(IAS)Wuhan UniversityWuhanHubei 430072China State Key Laboroatory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling RoodShanghai 200032China National Research Center for Carbohydrate Synthesis Jiangxi Normal UniversityNanchangJiangxi 330022China

The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C-H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction *** reaction can be carried out in undivided cell without the addition of external chemical *** good functional group compatibility,the desired carbazoles can be scaled up and modified *** with previous methods,this protocol affords a simple and sustainable avenue for the construction of car-bazoles.

关键词： Electrosynthesis palladium-catalyzed Cross coupling Amination Carbazoles