Surface-Controlled Mono/Diselective ortho C-H Bond Activation.
One of the most charming and challenging topics in organic chemistry is the selective C-H bond activation. The difficulty arises not only from the relatively large bond-dissociation enthalpy, but also from the poor reaction selectivity. In this work, Au(111) and Ag(111) surfaces were used to address...
| Publicado en: | Journal of the American Chemical Society Vol. 138; no. 8; pp. 2809 - 2815 |
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| Autores principales: | , , , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
3/2/2016
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=113856438&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 113856438 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 3/2/2016 vid: 138 iid: 8 pid: 997 pub: American Chemical Society artinfo: ui: 113856438 10.1021/jacs.5b13286 ppf: 2809 ppct: 6 formats: tig: atl: Surface-Controlled Mono/Diselective ortho C-H Bond Activation. aug: au: Qing Li Biao Yang Haiping Lin Nabi Aghdassi Kangjian Miao Junjie Zhang Haiming Zhang Youyong Li Steffen Duhm Jian Fan Lifeng Chi affil: Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, 199 Ren'ai Road, Suzhou, 215123, Jiangsu P. R. China su: Carbon-hydrogen bonds Dehydrogenation kinetics Density functional theory Organic synthesis Oxidation of phenol sug: subj: Carbon-hydrogen bonds Dehydrogenation kinetics Density functional theory Organic synthesis Oxidation of phenol ab: One of the most charming and challenging topics in organic chemistry is the selective C-H bond activation. The difficulty arises not only from the relatively large bond-dissociation enthalpy, but also from the poor reaction selectivity. In this work, Au(111) and Ag(111) surfaces were used to address ortho C-H functionalization and ortho-ortho couplings of phenol derivatives. More importantly, the competition between dehydrogenation and deoxygenation drove the diversity of reaction pathways of phenols on surfaces, that is, diselective ortho C-H bond activation on Au(111) surfaces and monoselective ortho C-H bond activation on Ag(111) surfaces. The mechanism of this unprecedented phenomenon was extensively explored by scanning tunneling microscopy, density function theory, and X-ray photoelectron spectroscopy. Our findings provide new pathways for surface-assisted organic synthesis via the mono/diselective C-H bond activation. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2016 holdings: @attributes: islocal: N |
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