Direct C-H arylation and alkenylation of 1-substituted tetrazoles: phosphine as stabilizing factor.
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.
Spulák
Marcel
M
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.
Lubojacký
Richard
R
Senel
Petr
P
Kunes
Jirí
J
Pour
Milan
M
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
D000475:Alkenes; D007093:Imidazoles; D008024:Ligands; D010720:Phosphines; D011687:Purines; D013777:Tetrazoles; D010165:Palladium; C044646:phosphine