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Palladium-catalyzed c-c Bond activation/Suzuki Reaction of Methylenecyclobutanes

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chinese Journal of chemistry 2021年第6期39卷 1611-1615页

作者： Xiao-Bing chen Li Li Wan-chun Yang Kun-Long Song Bin Wu Wan-Er Gan Jian cao Li-Wen Xu Key Laboratory of Organosilicon chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang ProvinceHangzhou Normal UniversityNo.2318Yuhangtong RoodHangzhouZhejiang 311121China State Key Laboratory for Oxo Synthesis and Selective Oxidation Suzhou Research Institute and Lonzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhouGansu 730000China

Transition-metal catalyzed c-c bond activation is a formidable challenge owing to the high bond *** report here a novel palladium-catalyzed c-c bond activation manner of methylenecyclobutanes followed by subsequent Suzuki cross-coupling reaction affording multisubstituted *** tandem reaction process involves intramolecular carbopalladation of double bond,β-carbon elimination and intermolecular trapping of the transient a-alkylpalladium complex with boronic acids.A new TADDOL-derived phos-phoramidite ligand bearing fluorine and silicon-based bulky groups is found to be efficient for c-c bond activation of methylenecyclobutanes.

关键词： c-c activation Palladium c-c coupling Ring-opening Methylenecyclobutanes

copper Promoted Deacylation of Ynones via c-c Bond activation under Mild Reaction conditions

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Copper Promoted Deacylation of Ynones via C-C Bond Activatio...

Ligand-controlled Palladium-catalyzed Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes viaσ-Bond activation

中国化学会·第十六届全国有机合成化学学术研讨会

作者： Lili Feng Tingjun Hu Saisai Zhang 张光武 Heng-Ying Xiong college of chemistry and chemical Engineering Henan University 河南大学

carbon-carbon single bonds are undoubtedly considered as one of the least reactive "functional" groups among a wide range of organic functionalities that can be activated by transition metal complexes. In this paper,the intermolecular deacylative coupling of unstrained ynones via c-c bond activation was realized by a cucl-bpy system at room temperature to access 1,3-diynes *** method demonstrates good functional group tolerance and wide substrate scope,and is applicable for homo and cross coupling of ynones,giving a range of substituted 1,3-diynes from moderate to excellent ***,the cyclization of selected 1,3-diynes with a sulfur source furnished2,5-disubstituted thiophenes, which are of great interest for material purpose.

关键词： deacylation c-c activation copper ynone 1,3-diynes

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chinese Journal of chemistry 2022年第19期40卷 2345-2355页

作者： Lei Wu Minyan Wang Yong Liang Zhuangzhi Shi State Key Laboratory of coordination chemistry School of Chemistry and Chemical EngineeringNanjing UniversityNanjingJiangsu210093 China School of chemistry and chemical Engineering Henan Normal UniversityXinxiangHenan453007 China

Monofluoroalkenes are important and versatile privileged components in pharmacologically relevant ***,we report a method for the selective construction of these compounds in a diversity-oriented fashion through regiodivergent cross-coupling of gem-difluorocyclopropanes with allylboronates by employing a palladium catalyst with two different ligands,in which gem-difluorocyclopropanes were used as allyl electrophiles by c—c and c—F bond *** the presence of 2-biphenylyl(diphenyl)phosphine as ligand,the linear-selective allyl–allyl bond formation is highly obtained,while utilizing the sterically hindered BrettPhos(dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine)as the ligand favors the generation of the branched-selective *** and computational studies investigated the key steps of the cross-coupling reactions,revealing the origin of the ligand-controlled regiodivergence.

关键词： Allylation c-c activation cross-coupling gem-Difluorocyclopropanes Defluorination

Graphene-Oxide Mediated chemodivergent Ring-Opening of cyclobutanols

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chinese Journal of chemistry 2023年第11期41卷 1333-1340页

作者： Andrea Brunetti Angela Pintus Lorenzo Lombardi Alessandro Kovtun Federico Mascietti Francesco Bruno Enrico Ravera Manuela Melucci Giulio Bertuzzi Marco Bandini Dipartimento di chimica“Giacomo ciamician” Alma Mater StudiorumUniversitàdi BolognaVia Selmi 240126BolognaItaly Istituto per la Sintesi e la Fotoreattività(ISOF)–cNR Via Gobetti10140129BolognaItaly Magnetic Resonance center(cERM) University of FlorenceVia L.Sacconi 650019 Sesto FiorentinoItaly Department of chemistry“Ugo Schiff” University of FlorenceVia della Lastruccia 350019 Sesto FiorentinoItaly center for chemical catalysis–c3 Alma Mater StudiorumUniversitàdi Bolognavia Selmi 240126BolognaItaly

The chemodivergent ring-opening of cyclobutanols is described under the carbocatalytic assistance of graphene oxide(GO).The protocol enables the synthesis of diversely functionalized dienes or indenes(26 examples)based on the amount of GO ***(XPS and ssNMR)as well as experimental investigations revealed a direct involvement of theπ-domains of GO in tuning the stability of carbocationic intermediates during the reaction.

关键词： carbocatalysis c-c activation Graphene carbocations Methodology and reactions

Palladium-catalyzed Skeletal Reorganization of cyclobutanones Invoving Successive c—c Bond/c—H Bond cleavage

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中国化学:英文版 2023年第14期41卷 1679-1683页

作者： Ruirui Li Xiaonan Shi Dongbing Zhao State Key Laboratory and Institute of Elemento-Organic chemistry College of ChemistryNankai UniversityTianjin300071 China

The utilization of cyclobutanones as the synthon in transition metal catalysis has been made great *** c(carbonyl)−c bond of cyclobutanones can be cleaved through strain *** those advancements,the main catalysts in literature are Rh catalysts or Ni catalysts and the reaction with c—H bond is still ***,we realized the first palladium-catalyzed skeletal reorganization of cyclobutanones involving successive cleavage of c(carbonyl)−c bonds and c—H bond cleavage,which constitutes an rapid access to diverse *** contrast to the previous Rh-catalytic system,the Pd-catalytic system herein involves different mechanism and features several advantages:1)no need of directing group to facilitate the c(carbonyl)−c bond cleavage;2)much milder reaction condition and 3)simplified work-up.

关键词： cyclobutanones c-c activation c-H activation Palladium catalysis Ring expansion

Selective carbon-carbon Bond Amination with Redox-Active Aminating Reagents:A Direct Approach to Anilines

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chinese Journal of chemistry 2021年第18期39卷 3011-3016页

作者： Xu Qiu Yachong Wang Lingyu Su Rui Jin Song Song Qixue Qin Junhua Li Baoning Zong Ning Jiao State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical SciencesPeking UniversityBeijing100191 China State Key Laboratory of catalytic Materials and Reaction Engineering Research Institute of Petroleum ProcessingSINOPEC100083 BeijingChina Shanghai Key Laboratory of Green chemistry and chemical Processes East China Normal UniversityShanghai200062 China

Amines are among the most fundamental motifs in chemical synthesis,and the introduction of amine building blocks via selective c-c bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton ***,we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents,which are easily prepared from *** amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild *** compatibility and valuable applications of the transformation were also displayed.

关键词： Anilines c-c activation Amination Nitrogenation Arenes