title: Palladium-catalyzed imidoylative cyclization of α-isocyanoacetamides: efficient access to C2-diversified oxazoles.
abstract: A novel procedure for the synthesis of C2-diversified oxazoles, through palladium-catalyzed imidoylative cyclization of α-isocyanoacetamides with aryl, vinyl, alkynyl halides, or triflates, was developed. Migratory insertion of isocyanide into a Csp3-palladium(II) intermediate in a cascade process was also realized, generating alkyl-substituted oxazoles. Therefore, oxazoles functionalized at the C2 position with sp, sp(2), and sp(3) hybridized carbon atoms are accessible by applying this method.
authors.affiliation: State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (P.R. China), Fax: (+86) 20-3201-5299.
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
authors.forename: Shuang
authors.initials: S
authors.lastname: Luo
authors.forename: Jinbo
authors.initials: J
authors.lastname: Huang
authors.forename: Tingting
authors.initials: T
authors.lastname: Mao
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhu
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D007094:Imides; D009570:Nitriles; D010080:Oxazoles; D010165:Palladium; C031594:2-cyanoacetamide
keywords: heterocycles; imidoylative cyclization; oxazoles; palladium; α-isocyanoacetamide