title: Direct C-H arylation and alkenylation of 1-substituted tetrazoles: phosphine as stabilizing factor.
abstract: Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs(2)CO(3). Unlike the related reactions of imidazoles and purines, phosphine ligand was necessary to prevent the intermediate tetrazolyl-Pd(II) species from fragmentation into the corresponding cyanamide. Various 1,5-disubstituted tetrazoles were prepared with good to excellent isolated yields.
authors.affiliation: Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, CZ-500 03 Hradec Králové, Czech Republic.
authors.forename: Marcel
authors.initials: M
authors.lastname: Spulák
authors.forename: Richard
authors.initials: R
authors.lastname: Lubojacký
authors.forename: Petr
authors.initials: P
authors.lastname: Senel
authors.forename: Jirí
authors.initials: J
authors.lastname: Kunes
authors.forename: Milan
authors.initials: M
authors.lastname: Pour
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D011687:Purines / Q000737:chemistry; D013237:Stereoisomerism; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D007093:Imidazoles; D008024:Ligands; D010720:Phosphines; D011687:Purines; D013777:Tetrazoles; D010165:Palladium; C044646:phosphine