Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C-H Borylation of Substituted Arenes and 5-Membered Heterocycles.
The iridium-catalyzed borylation of mono- and disubstituted arenes and heteroarenes has been studied with density functional theory. The distortion/interaction model was employed to understand the origins of selectivities in these reactions. Computations revealed that the transition states for C-H o...
| Publicado en: | Journal of the American Chemical Society Vol. 136; no. 12; pp. 4575 - 4584 |
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| Autores principales: | , , , |
| Formato: | Artículo |
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American Chemical Society
3/26/2014
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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=95575368&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 95575368 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: 3/26/2014 vid: 136 iid: 12 pid: 997 pub: American Chemical Society artinfo: ui: 95575368 10.1021/ja411699u ppf: 4575 ppct: 9 formats: tig: atl: Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C-H Borylation of Substituted Arenes and 5-Membered Heterocycles. aug: au: Green, Aaron G. Peng Liu Merlic, Craig A. Houk, K. N. affil: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States su: Iridium catalysts Density functional theory Carbon-hydrogen bonds Heteroarenes Aromatic compounds Transition state theory (Chemistry) Oxidative addition Regioselectivity (Chemistry) sug: subj: Iridium catalysts Density functional theory Carbon-hydrogen bonds Heteroarenes Aromatic compounds Transition state theory (Chemistry) Oxidative addition Regioselectivity (Chemistry) ab: The iridium-catalyzed borylation of mono- and disubstituted arenes and heteroarenes has been studied with density functional theory. The distortion/interaction model was employed to understand the origins of selectivities in these reactions. Computations revealed that the transition states for C-H oxidative addition are very late, resembling the aryl iridium hydride intermediate with a fully formed Ir-C bond. Consequently, the regioselectivity is mainly controlled by differences in the interaction energies between the iridium catalyst and arene carbon. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2014 holdings: @attributes: islocal: N |
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