Direct C-H arylation and alkenylation of 1-substituted tetrazoles: phosphine as stabilizing factor.

J Org Chem

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.

Published: January 2010

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.

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http://dx.doi.org/10.1021/jo902180uDOI Listing

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