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Enhancement of Neighbouring-Group Participation in Cu-0-Promoted Cross-Coupling gem-Difluoromethylenation of Aryl/Alkenyl Halides with 1,3-Azolic Difluoromethyl Bromides
Alternative Title铜催化gem-Difluoromethylenation的不饱和卤化物和1,3-Azolic Difluoromethyl Bromides的交叉耦合反应中的邻位增强作用
Jiang HZ(蒋海珍)1; LU WENJUN1; YANG KUN1; MA GUOBIN1; XU MINJUN1; Li J(李佳)1; Yao JH(姚建华)1; WAN WEN1; DENG HONGMEI1; WU SHAOXIONG1; Zhu SZ(朱仕正)1; HAO JIAN1
2014
Source PublicationChem.-Eur. J.
Volume20Issue:32Pages:10084-10092
AbstractA copper(0)-promoted direct reductive gem-difluoromethylenation of unactivated aryl or alkenyl halides with benzo-1,3-azolic (oxa-, thia- or aza-) difluoromethyl bromides or 2-bromodifluoromethyl-1,3-oxazoline has been developed for the construction of pharmaceutically important gem-difluoromethylene-linked twin molecules. The unique p-conjugated aryl-fused 1,3-azolic moiety in difluoromethyl bromide substrates could stabilise the reaction intermediates, which promotes the reactivities, providing facile access to the cross-coupling products in good to excellent yields, and allowing significant functional group tolerance. The reaction exhibits an enhanced neighbouring-group-participation effect. This method could provide a new strategy for the construction of gem-difluoromethylene-linked identical or nonidentical twin drugs through further functionalisation of 1,3-azolic skeletons.
Subject Area有机化学
DOI10.1002/chem.201402205
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Indexed BySCI
Language英语
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Cited Times:23[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39165
Collection上海有机化学研究所
Corresponding AuthorJiang HZ(蒋海珍); Zhu SZ(朱仕正); HAO JIAN
Affiliation1.上海大学
2.中科院上海有机化学研究所
3.美国艾默里大学
Recommended Citation
GB/T 7714
Jiang HZ,LU WENJUN,YANG KUN,et al. Enhancement of Neighbouring-Group Participation in Cu-0-Promoted Cross-Coupling gem-Difluoromethylenation of Aryl/Alkenyl Halides with 1,3-Azolic Difluoromethyl Bromides[J]. Chem.-Eur. J.,2014,20(32):10084-10092.
APA 蒋海珍.,LU WENJUN.,YANG KUN.,MA GUOBIN.,XU MINJUN.,...&HAO JIAN.(2014).Enhancement of Neighbouring-Group Participation in Cu-0-Promoted Cross-Coupling gem-Difluoromethylenation of Aryl/Alkenyl Halides with 1,3-Azolic Difluoromethyl Bromides.Chem.-Eur. J.,20(32),10084-10092.
MLA 蒋海珍,et al."Enhancement of Neighbouring-Group Participation in Cu-0-Promoted Cross-Coupling gem-Difluoromethylenation of Aryl/Alkenyl Halides with 1,3-Azolic Difluoromethyl Bromides".Chem.-Eur. J. 20.32(2014):10084-10092.
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