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Ligand-Controlled Palladium-Catalyzed Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes viaσ-Bond Activation

查看全文 作　　者：Lei [1]Wu;Minyan [1]Wang;Yong [1]Liang;Zhuangzhi [1,2]Shi 高影响力作者 机构地区：[1]State Key Laboratory of Coordination Chemistry,School of Chemistry and Chemical Engineering,Nanjing University,Nanjing,Jiangsu,210093 China;[2]School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang,Henan,453007 China高影响力机构 出　　处：《Chinese Journal of Chemistry》索引2022年第40卷第19期,共11页高影响力期刊 基　　金：the National Natural Science Foundation of China(Grants 22025104,21972064 and 21901111);the Fundamental Research Funds for the Central Universities for their financial support(Grant 020514380254);The project was also supported by Open Research Fund of School of Chemistry and Chemical Engineering,Henan Normal University. 摘　　要：Monofluoroalkenes are important and versatile privileged components in pharmacologically relevant molecules.Here,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 activation.In 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 product.Experimental 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
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