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Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines
Wang, Quannan1,2; Lou, Jiang1,2; Huang, Zilong1,2; Yu, Zhengkun1,3
Corresponding AuthorYu, Zhengkun(zkyu@dicp.ac.cn)
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2019-02-15
ISSN0022-3263
DOI10.1021/acs.joc.8b03092
Volume84Issue:4Pages:2083-2092
Funding ProjectNational Natural Science Foundation of China[21871253] ; National Natural Science Foundation of China[21472185] ; National Basic Research Program of China[2015CB856600]
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordREGIOSELECTIVE INTERMOLECULAR ANNULATION ; BOND ACTIVATION ; ASYMMETRIC-SYNTHESIS ; DIRECT ARYLATION ; ALLENES ; FUNCTIONALIZATION ; ALLYLATION ; ALKYNES ; DECARBONYLATION ; SULFONAMIDES
AbstractRhodium(III)-catalyzed annulation of acetophenone O-acetyl oximes with allenoates was achieved, affording isoquinolines in good to excellent yields with high regioselectivities under redox-neutral conditions. Allenoates acted as the C2 synthons in the annulation reaction. The present synthetic methodology features good functional group tolerance and avoids metal salts as the external oxidants. The proposed mechanism suggests that the reaction proceeds through arene C-H activation, allene insertion, and C-N coupling.
Language英语
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Basic Research Program of China ; National Basic Research Program of China
WOS IDWOS:000459367100041
PublisherAMER CHEMICAL SOC
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Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/165797
Collection中国科学院大连化学物理研究所
Corresponding AuthorYu, Zhengkun
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
Wang, Quannan,Lou, Jiang,Huang, Zilong,et al. Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(4):2083-2092.
APA Wang, Quannan,Lou, Jiang,Huang, Zilong,&Yu, Zhengkun.(2019).Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines.JOURNAL OF ORGANIC CHEMISTRY,84(4),2083-2092.
MLA Wang, Quannan,et al."Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines".JOURNAL OF ORGANIC CHEMISTRY 84.4(2019):2083-2092.
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