title: Transition-metal-free α-arylation of β-keto amides via an interrupted insertion reaction of arynes.
abstract: Direct α-arylation reactions of secondary β-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, are described. The transformation proceeds via an interrupted insertion reaction of arynes and leads to densely functionalized aromatic compounds exhibiting a chiral 'all carbon' quaternary center under transition-metal-free conditions. An organocatalytic asymmetric version of the reaction also proved possible, affording the proof of concept that arynes can be involved in enantioselective transformations.
authors.affiliation: Aix-Marseille Université, CNRS, iSm2 UMR 7313, Service 531, 13397 Marseille cedex 20, France.
authors.forename: Kishor
authors.initials: K
authors.lastname: Mohanan
authors.forename: Yoann
authors.initials: Y
authors.lastname: Coquerel
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
mesh_terms: D000577:Amides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism; D028561:Transition Elements
chemical_list: D000577:Amides; D001555:Benzene Derivatives; D028561:Transition Elements; C524146:benzyne