DICP OpenIR
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
Bai, Dachang1; Xia, Jintao2,4; Song, Fangfang1; Li, Xueyan1; Liu, Bingxian1; Liu, Lihong1; Zheng, Guangfan3; Yang, Xifa; Sun, Jiaqiong3; Li, Xingwei1,2
Corresponding AuthorSun, Jiaqiong(sunjq295@nenu.edu.cn) ; Li, Xingwei(xwli@dicp.ac.cn)
Source PublicationCHEMICAL SCIENCE
2019-04-14
ISSN2041-6520
DOI10.1039/c9sc00545e
Volume10Issue:14Pages:3987-3993
Funding ProjectNSFC[21525208] ; NSFC[21801067] ; Henan Normal University[5101034011009] ; Henan Normal University[qd17108] ; Education Department of Henan Province Natural Science Research Program[18A150010]
Funding OrganizationNSFC ; 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
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordONE-POT SYNTHESIS ; INTERNAL ALKYNES ; BOND ACTIVATION ; RH(III)-CATALYZED SYNTHESIS ; OXIDATIVE ANNULATIONS ; ISOQUINOLINIUM SALTS ; CATALYZED ANNULATION ; 1,4-METAL MIGRATION ; COUPLING REACTIONS ; N-OXIDES
AbstractNitrogen-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.
Language英语
Funding OrganizationNSFC ; 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
WOS IDWOS:000467988600006
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/171932
Collection中国科学院大连化学物理研究所
Corresponding AuthorSun, Jiaqiong; Li, Xingwei
Affiliation1.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
Recommended Citation
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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