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Catalyst-Controlled Regiodivergent Alkyne Insertion in the Context of C-H Activation and Diels-Alder Reactions: Synthesis of Fused and Bridged Cycles
Zhou, Xukai1,2; Pan, Yupeng1; Li, Xingwei1
KeywordC-h Activation Cobalt Cycloadditions Polycycles Rhodium
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2017-07-03
DOI10.1002/anie.201704036
Volume56Pages:8163-8167
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordONE-POT SYNTHESIS ; N-TYPE REACTIONS ; INTERNAL ALKYNES ; TERMINAL ALKYNES ; ARYLATIVE CYCLIZATION ; INDOLE SYNTHESIS ; BOND ACTIVATION ; ANNULATION ; ARENES ; FUNCTIONALIZATION
AbstractRhodium(III) -and cobalt(III)-catalyzed C-H activation of indoles and coupling with 1,6-enynes is discussed. Under rhodium(III) catalysis, the alkyne insertion follows 2,1-regioselectivity with a subsequent type-I intramolecular Diels-Alder reaction (IMDA) to afford [6,5]-fused cycles. When catalyzed by the cobalt(III) congener, 1,2-insertion of the alkyne is preferred, and followed by a rare type-II IMDA, thus leading to bridged [3,3,1]-cycles. This selectivity of the alkyne insertion was mainly tuned by the steric sensitivity of the catalyst.
Language英语
WOS IDWOS:000404140900021
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/152100
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhou, Xukai,Pan, Yupeng,Li, Xingwei. Catalyst-Controlled Regiodivergent Alkyne Insertion in the Context of C-H Activation and Diels-Alder Reactions: Synthesis of Fused and Bridged Cycles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56:8163-8167.
APA Zhou, Xukai,Pan, Yupeng,&Li, Xingwei.(2017).Catalyst-Controlled Regiodivergent Alkyne Insertion in the Context of C-H Activation and Diels-Alder Reactions: Synthesis of Fused and Bridged Cycles.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56,8163-8167.
MLA Zhou, Xukai,et al."Catalyst-Controlled Regiodivergent Alkyne Insertion in the Context of C-H Activation and Diels-Alder Reactions: Synthesis of Fused and Bridged Cycles".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56(2017):8163-8167.
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