Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles.
A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1- bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at —70 °C. In the subsequent reactor o-bromop...
| Publicado en: | Journal of the American Chemical Society Vol. 136; no. 35; pp. 12245 - 12249 |
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| Autores principales: | , , |
| Formato: | Artículo |
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American Chemical Society
9/3/2014
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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=98363383&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 98363383 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: 9/3/2014 vid: 136 iid: 35 pid: 997 pub: American Chemical Society artinfo: ui: 98363383 10.1021/ja5071762 ppf: 12245 ppct: 4 formats: tig: atl: Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles. aug: au: Aiichiro Nagaki Daisuke Ichinari Jun-ichi Yoshida affil: Department of Synthetic Chemistry & Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan su: Benzynes Electrophiles Microreactors Aryl halides Chemical decomposition Biogeochemical residence time Chemical reactions sug: subj: Benzynes Electrophiles Microreactors Aryl halides Chemical decomposition Biogeochemical residence time Chemical reactions ab: A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1- bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at —70 °C. In the subsequent reactor o-bromophenyllithium is decomposed to generate benzyne without affecting the functionalized aryllithium at —30 °C, and carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature-residence time mapping is responsible for the success of the present transformation. The present method has been successfully applied to the synthesis of boscalid. 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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