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Identifying key intermediates generated in situ from cu(ii) salt-catalyzed c-h functionalization of aromatic amines under illumination
Meng, Qing-Yuan1,2; Gao, Xue-Wang1,2; Lei, Tao1,2; Liu, Zan1,2; Zhan, Fei3; Li, Zhi-Jun1,2; Zhong, Jian-Ji1,2; Xiao, Hongyan1,2; Feng, Ke1,2; Chen, Bin1,2
刊名Science advances
2017-08-01
卷号3期号:8页码:10
ISSN号2375-2548
DOI10.1126/sciadv.1700666
通讯作者Wu, li-zhu(lzwu@mail.ipc.ac.cn)
英文摘要Copper 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.
WOS关键词TRANSFER RADICAL-ADDITION ; VISIBLE-LIGHT PHOTOREDOX ; ROOM-TEMPERATURE ; ELECTRON-TRANSFER ; CROSS-COUPLINGS ; GLYCINE DERIVATIVES ; VERSATILE APPROACH ; ORGANIC-SYNTHESIS ; ALKYL-HALIDES ; COPPER
WOS研究方向Science & Technology - Other Topics
WOS类目Multidisciplinary Sciences
语种英语
出版者AMER ASSOC ADVANCEMENT SCIENCE
WOS记录号WOS:000411589900056
内容类型期刊论文
URI标识http://www.corc.org.cn/handle/1471x/2177071
专题高能物理研究所
通讯作者Wu, Li-Zhu
作者单位1.Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
2.Chinese Acad Sci, Univ Chinese Acad Sci, Beijing 100190, Peoples R China
3.Chinese Acad Sci, Beijing Synchrotron Radiat Facil, Inst High Energy Phys, Beijing 100039, Peoples R China
推荐引用方式
GB/T 7714
Meng, Qing-Yuan,Gao, Xue-Wang,Lei, Tao,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):10.
APA Meng, Qing-Yuan.,Gao, Xue-Wang.,Lei, Tao.,Liu, Zan.,Zhan, Fei.,...&Wu, Li-Zhu.(2017).Identifying key intermediates generated in situ from cu(ii) salt-catalyzed c-h functionalization of aromatic amines under illumination.Science advances,3(8),10.
MLA Meng, Qing-Yuan,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):10.
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