title: Exploiting Deep Eutectic Solvents and Organolithium Reagent Partnerships: Chemoselective Ultrafast Addition to Imines and Quinolines Under Aerobic Ambient Temperature Conditions.
abstract: Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds. Comparing RLi reactivities in DESs with those observed in pure glycerol or THF suggests a kinetic anionic activation of the alkylating reagents occurs, favoring nucleophilic addition over competitive hydrolysis.
authors.affiliation: Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Departamento de Química Orgánica e Inorgánica (IUQOEM), Facultad de Química, Universidad de Oviedo, 33071, Oviedo, Spain.
authors.forename: Cristian
authors.initials: C
authors.lastname: Vidal
authors.affiliation: Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Departamento de Química Orgánica e Inorgánica (IUQOEM), Facultad de Química, Universidad de Oviedo, 33071, Oviedo, Spain.
authors.forename: Joaquín
authors.initials: J
authors.lastname: García-Álvarez
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: Alberto
authors.initials: A
authors.lastname: Hernán-Gómez
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: Eva
authors.initials: E
authors.lastname: Hevia
keywords: deep eutectic solvents; green chemistry; imines; organolithium reagents; salt activation