title: Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups.
abstract: In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).
authors.affiliation: AstraZeneca R&D Mölndal, Pepparedsleden 1, 43183 Mölndal, Sweden. gavin.omahony@astrazeneca.com
authors.forename: Gavin
authors.initials: G
authors.lastname: O'Mahony
authors.forename: Andrew K
authors.initials: AK
authors.lastname: Pitts
mesh_terms: D000577:Amides / Q000737:chemistry*; D006858:Hydrofluoric Acid / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000577:Amides; D014867:Water; D006858:Hydrofluoric Acid