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Identifying key intermediates generated in situ from Cu(II) salt-catalyzed C-H functionalization of aromatic amines under illumination
Meng, QY; Gao, XW; Lei, T; Liu, Z; Zhan, F; Li, ZJ; Zhong, JJ; Xiao, HY; Feng, K; Chen, B; Tao, Y; Tung, CH; Wu, LZ; Tao Y(陶冶)
2017
Source PublicationSCIENCE ADVANCES
ISSN2375-2548
Volume3Issue:8Pages:e1700666
SubtypeArticle
AbstractCopper compounds involved in photocatalysis have recently spurred considerable interest for their novel transformations. However, mechanistic investigations are still in infancy. We find a new type of reaction, that is, Cu(II) salt-catalyzed C-H functionalization of aromatic amines triggered by visible light irradiation. An array of mechanistic observations, including high-resolution mass spectrometry, ultraviolet-visible absorption spectrum, electron spin resonance, x-ray absorption near-edge structure, and density functional theory calculation, have identified the key intermediates generated in situ in the transformation. Integration of single-electron transfer, singlet oxygen (O-1(2)), and new absorption species, intermediate I and intermediate II formed in situ from Cu( II) salts and substrate amines or imines, respectively, is responsible for the N-H and C-H bond activation of secondary amines to couple with nucleophiles in air, thereby leading to the formation of quinoline, indolo[3,2-c] quinoline, beta-amino acid, and 1,4-dihydropyridine derivatives in moderate to good yields under visible light irradiation at room temperature.
DOI10.1126/sciadv.1700666
WOS KeywordTRANSFER RADICAL-ADDITION ; VISIBLE-LIGHT PHOTOREDOX ; ROOM-TEMPERATURE ; ELECTRON-TRANSFER ; CROSS-COUPLINGS ; GLYCINE DERIVATIVES ; VERSATILE APPROACH ; ORGANIC-SYNTHESIS ; ALKYL-HALIDES ; COPPER
Indexed BySCI ; EI ; PUBMED ; SCOPUS ; ADS
Language英语
WOS Research AreaScience & Technology - Other Topics
WOS SubjectMultidisciplinary Sciences
WOS IDWOS:000411589900056
EI Accession Number20180704796700
EI KeywordsAbsorption spectroscopy - Amines - Aromatic compounds - Catalysis - Chemical bonds - Density functional theory - Electron spin resonance spectroscopy - Irradiation - Light - Magnetic moments - Mass spectrometry - X ray absorption - X ray absorption near edge structure spectroscopy
EI Classification Number701.2 Magnetism: Basic Concepts and Phenomena - 711 Electromagnetic Waves - 741.1 Light/Optics - 801 Chemistry - 801.4 Physical Chemistry - 802.2 Chemical Reactions - 804.1 Organic Compounds - 931.3 Atomic and Molecular Physics
ADS Bibcode2017SciA....3E0666M
ADS URLhttps://ui.adsabs.harvard.edu/abs/2017SciA....3E0666M
ADS CITATIONShttps://ui.adsabs.harvard.edu/abs/2017SciA....3E0666M/citations
Citation statistics
Cited Times:3 [ADS]
Document Type期刊论文
Identifierhttp://ir.ihep.ac.cn/handle/311005/284927
Collection多学科研究中心
加速器中心
Affiliation中国科学院高能物理研究所
First Author AffilicationInstitute of High Energy
Recommended Citation
GB/T 7714
Meng, QY,Gao, XW,Lei, T,et al. Identifying key intermediates generated in situ from Cu(II) salt-catalyzed C-H functionalization of aromatic amines under illumination[J]. SCIENCE ADVANCES,2017,3(8):e1700666.
APA Meng, QY.,Gao, XW.,Lei, T.,Liu, Z.,Zhan, F.,...&陶冶.(2017).Identifying key intermediates generated in situ from Cu(II) salt-catalyzed C-H functionalization of aromatic amines under illumination.SCIENCE ADVANCES,3(8),e1700666.
MLA Meng, QY,et al."Identifying key intermediates generated in situ from Cu(II) salt-catalyzed C-H functionalization of aromatic amines under illumination".SCIENCE ADVANCES 3.8(2017):e1700666.
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