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Rhodium(iii)-catalyzed diverse [4+1] annulation of arenes with 1,3-enynes via sp(3)/sp(2) C-H activation and 1,4-rhodium migration

文献类型：期刊论文

作者Bai, Dachang1; Xia, Jintao2,4; Song, Fangfang1; Li, Xueyan1; Liu, Bingxian1; Liu, Lihong1; Zheng, Guangfan3; Yang, Xifa; Sun, Jiaqiong3; Li, Xingwei1,2
刊名CHEMICAL SCIENCE
出版日期2019-04-14
卷号10期号:14页码:3987-3993
ISSN号2041-6520
DOI10.1039/c9sc00545e
通讯作者Sun, Jiaqiong(sunjq295@nenu.edu.cn) ; Li, Xingwei(xwli@dicp.ac.cn)
英文摘要Nitrogen-rich heterocyclic compounds have a profound impact on human health. Despite the numerous synthetic methods, diversified, step-economic, and general synthesis of heterocycles remains limited. C-H bond functionalization catalyzed by rhodium(iii) cyclopentadienyls has proven to be a powerful strategy in the synthesis of diversified heterocycles. Herein we describe rhodium(iii)-catalyzed sp(2) and sp(3) C-H activation-oxidative annulations between aromatic substrates and 1,3-enynes, where alkenyl-to-allyl 1,4-rhodium(iii) migration enabled the generation of electrophilic rhodium(iii) -allyls via remote C-H functionalization. Subsequent nucleophilic trapping of these species by various sp(2)-hybridized N-nucleophiles delivered three classes (external salts, inner salts, and neutral azacycles) of five-membered azacycles bearing a tetrasubstituted saturated carbon center, as a result of [4 + 1] annulation with the alkyne being a one-carbon synthon. All the reactions proceeded under relatively mild conditions with broad substrate scope, high efficiency, and excellent regioselectivity. The synthetic applications of this protocol have also been demonstrated, and experimental studies have been performed to support the proposed mechanism.
WOS关键词ONE-POT SYNTHESIS ; INTERNAL ALKYNES ; BOND ACTIVATION ; RH(III)-CATALYZED SYNTHESIS ; OXIDATIVE ANNULATIONS ; ISOQUINOLINIUM SALTS ; CATALYZED ANNULATION ; 1,4-METAL MIGRATION ; COUPLING REACTIONS ; N-OXIDES
资助项目NSFC[21525208] ; NSFC[21801067] ; Henan Normal University[5101034011009] ; Henan Normal University[qd17108] ; Education Department of Henan Province Natural Science Research Program[18A150010]
WOS研究方向Chemistry
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000467988600006
资助机构NSFC ; NSFC ; Henan Normal University ; Henan Normal University ; Education Department of Henan Province Natural Science Research Program ; Education Department of Henan Province Natural Science Research Program ; NSFC ; NSFC ; Henan Normal University ; Henan Normal University ; Education Department of Henan Province Natural Science Research Program ; Education Department of Henan Province Natural Science Research Program ; NSFC ; NSFC ; Henan Normal University ; Henan Normal University ; Education Department of Henan Province Natural Science Research Program ; Education Department of Henan Province Natural Science Research Program ; NSFC ; NSFC ; Henan Normal University ; Henan Normal University ; Education Department of Henan Province Natural Science Research Program ; Education Department of Henan Province Natural Science Research Program
源URL[http://cas-ir.dicp.ac.cn/handle/321008/171931]  
专题大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者Sun, Jiaqiong; Li, Xingwei
作者单位1.Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
3.Shaanxi Normal Univ SNNU, Sch Chem & Chem Engn, Xian 710062, Shaanxi, Peoples R China
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Bai, Dachang,Xia, Jintao,Song, Fangfang,et al. Rhodium(iii)-catalyzed diverse [4+1] annulation of arenes with 1,3-enynes via sp(3)/sp(2) C-H activation and 1,4-rhodium migration[J]. CHEMICAL SCIENCE,2019,10(14):3987-3993.
APA Bai, Dachang.,Xia, Jintao.,Song, Fangfang.,Li, Xueyan.,Liu, Bingxian.,...&Li, Xingwei.(2019).Rhodium(iii)-catalyzed diverse [4+1] annulation of arenes with 1,3-enynes via sp(3)/sp(2) C-H activation and 1,4-rhodium migration.CHEMICAL SCIENCE,10(14),3987-3993.
MLA Bai, Dachang,et al."Rhodium(iii)-catalyzed diverse [4+1] annulation of arenes with 1,3-enynes via sp(3)/sp(2) C-H activation and 1,4-rhodium migration".CHEMICAL SCIENCE 10.14(2019):3987-3993.

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来源：大连化学物理研究所

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