Functionalization of p-activated alcohols by trapping carbocations in pure water under smooth conditions

Ortiz, R. ; Koukouras, A. ; Marqués-López, E. (Universidad de Zaragoza) ; Pérez Herrera, R. (Universidad de Zaragoza)

Resumen: Acetic acid as catalyst in pure water was found to be an excellent reaction medium for the direct dehydrative functionalization of p-activated alcohols using a wide variety of interesting C-, P-, and S-centered nucleophiles, such as indoles, pyrrole, anilines, 1, 3-dicarbonyl compounds, diphenyl phosphite and pyridine-2-thiol. The smooth reaction conditions, along with high yields, short reaction times, clean reaction crudes, an easy product isolation procedure, plus the reusability of the catalyst and the use of no excess of nucleophiles, make this approach an atom economical, green and appealing method to efficiently trap carbocations in pure water, leading to new Csp3 X bonds (X = Csp2, Csp3, P and S).

Idioma: Inglés

DOI: 10.1016/j.arabjc.2018.01.022

Año: 2019

Publicado en: ARABIAN JOURNAL OF CHEMISTRY 13, 1 (2019), 1866-1873
ISSN: 1878-5352

Factor impacto JCR: 4.762 (2019)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 45 / 177 = 0.254 (2019) - Q2 - T1

Factor impacto SCIMAGO: 0.779 - Chemistry (miscellaneous) (Q1) - Chemical Engineering (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E104
Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E77
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)