C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes.
C-N cross-coupling is an important class of reactions with far-reaching impacts across chemistry, materials science, biology, and medicine. Transition metal complexes can elegantly orchestrate diverse aminations but typically require demanding reaction conditions, precious metal catalysts, or oxygen...
| Publicado en: | Journal of the American Chemical Society Vol. 140; no. 24; pp. 7667 - 7674 |
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| Autores principales: | , , , |
| Formato: | Artículo |
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American Chemical Society
6/20/2018
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| 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=130322045&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 130322045 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: 6/20/2018 vid: 140 iid: 24 pid: 997 pub: American Chemical Society artinfo: ui: 130322045 10.1021/jacs.8b03744 ppf: 7667 ppct: 7 formats: tig: atl: C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes. aug: au: Chern-Hooi Lim Kudisch, Max Bin Liu Miyake, Garret M. affil: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States su: Photoexcitation Transition metal complexes Metal catalysts Irradiation Density functional theory sug: subj: Photoexcitation Transition metal complexes Metal catalysts Irradiation Density functional theory ab: C-N cross-coupling is an important class of reactions with far-reaching impacts across chemistry, materials science, biology, and medicine. Transition metal complexes can elegantly orchestrate diverse aminations but typically require demanding reaction conditions, precious metal catalysts, or oxygen-sensitive procedures. Here, we introduce a mild nickel-catalyzed C-N cross-coupling methodology that operates at room temperature using an inexpensive nickel source (NiBr·3HO), is oxygen tolerant, and proceeds through direct irradiation of the nickel-amine complex. This operationally robust process was employed for the synthesis of diverse C-N-coupled products (40 examples) by irradiating a solution containing an amine, an aryl halide, and a catalytic amount of NiBr·3HO with a commercially available 365 nm LED at room temperature without added photoredox catalyst and the amine substrate serving additional roles as the ligands and base. Density functional theory calculations and kinetic isotope effect experiments were performed to elucidate the observed C-N cross-coupling reactivity. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2018 holdings: @attributes: islocal: N |
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