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Página principal > Artículos > Artículos publicados > Stepwise Mechanism for the Bromination of Arenes by a Hypervalent Iodine Reagent |
Fecha: | 2020 |
Resumen: | A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring. |
Ayudas: | Agencia Estatal de Investigación CTQ2017-86936-P Agencia Estatal de Investigación CTQ2016-80375-P Agencia Estatal de Investigación RTI2018-097853-B-I00 Agencia Estatal de Investigación CTQ2016-81797-REDC Agencia Estatal de Investigación RED2018-102387-T Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR-465 |
Derechos: | Tots els drets reservats. |
Lengua: | Anglès |
Documento: | Article ; recerca ; Versió acceptada per publicar |
Publicado en: | Journal of organic chemistry, Vol. 85, Issue 4 (February 2020) , p. 2142-2150, ISSN 1520-6904 |
Postprint 26 p, 1.0 MB |