title: Sustainable synthesis of diverse privileged heterocycles by palladium-catalyzed aerobic oxidative isocyanide insertion.
abstract: O(2) in, H(2)O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)(2) (1 mol %) as the catalyst and O(2) as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility of this highly sustainable method is demonstrated by a formal synthesis of the antihistamines astemizole and norastemizole.
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences, VU University Amsterdam, The Netherlands.
authors.forename: Tjøstil
authors.initials: T
authors.lastname: Vlaar
authors.forename: Razvan C
authors.initials: RC
authors.lastname: Cioc
authors.forename: Pieter
authors.initials: P
authors.lastname: Mampuys
authors.forename: Bert U W
authors.initials: BU
authors.lastname: Maes
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
mesh_terms: D016589:Astemizole / Q000138:chemical synthesis / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry; D006146:Guanidines / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001562:Benzimidazoles; D003486:Cyanides; D003959:Diamines; D006146:Guanidines; D006571:Heterocyclic Compounds; D010880:Piperidines; D010165:Palladium; D016589:Astemizole; C106448:tecastemizole