Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations -- New Method for the Synthesis of Pyrroloindolines.
Herein, we report the first examples of the synthesis of pyrroloindolines by means of (3 + 2) dearomative annulation reactions between 3-substituted indoles and highly reactive azaoxyallyl cations. Computational studies using density functional theory (DFT) (B3LYP-D3/6-311G**++) support a stepwise r...
| Publicado en: | Journal of the American Chemical Society Vol. 137; no. 47; pp. 14861 - 14865 |
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| Autores principales: | , , |
| Formato: | Artículo |
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American Chemical Society
12/2/2015
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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=111895164&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 111895164 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: 12/2/2015 vid: 137 iid: 47 pid: 997 pub: American Chemical Society artinfo: ui: 111895164 10.1021/jacs.5b10221 ppf: 14861 ppct: 4 formats: tig: atl: Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations -- New Method for the Synthesis of Pyrroloindolines. aug: au: DiPoto, Maria C. Hughes, Russell P. Wu, Jimmy affil: Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, United States su: Indoline Cations Annulation Density functional theory Carbon-carbon bonds sug: subj: Indoline Cations Annulation Density functional theory Carbon-carbon bonds ab: Herein, we report the first examples of the synthesis of pyrroloindolines by means of (3 + 2) dearomative annulation reactions between 3-substituted indoles and highly reactive azaoxyallyl cations. Computational studies using density functional theory (DFT) (B3LYP-D3/6-311G**++) support a stepwise reaction pathway in which initial C-C bond formation takes place at C3 of indole, followed by ring closure to give the observed products. Insights gleaned from these calculations indicate that the solvent, either TFE or HFIP, can stabilize the transition state through H-bonding interactions with oxygen of the azaoxyallyl cation and other relevant intermediates, thereby increasing the rates of these reactions. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2015 holdings: @attributes: islocal: N |
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