An efﬁcient synthesis of 5-substituted 1H-tetrazoles
catalyzed by graphene
Received: 3 March 2013 / Accepted: 4 May 2013 / Published online: 25 May 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract We report an efﬁcient method of synthesis of 5-substituted 1H-tetrazoles
by [2?3] cycloaddition of nitriles and sodium azide with graphene as nonmetal
catalyst. Under optimized conditions, moderate to good yields (60–70 %) are
obtained. The catalyst can be easily separated by centrifugation.
Keywords Graphene Á Tetrazole Á [2?3] Cycloaddition
Tetrazoles can be regarded as biologically equivalent to the carboxylic acid group,
and intensive research is currently being conducted on tetrazoles, mainly because of
their wide range of applications . Conventional methods of synthesis of tetrazoles
have disadvantages, including use of expensive and toxic metals . Tetrazoles are
usually synthesized from nitriles and sodium azides . This reaction can also be
performed with TMS-N
and TBAF instead of metal salts under solvent-free
conditions , or in micellar media  or an ionic liquid .
Graphene is one of the most exciting materials being investigated today . It is a two-
dimension material composed of layers of carbon atoms forming six-membered rings.
Many properties of graphene have been investigated, for example electrical, magnetic,
and others . Our group is interested in developing nonmetal catalysts, for example
graphene, to prepare tetrazoles with high yields in heterogeneous catalytic systems.
Nonmetal catalysts have never been reported for preparation of tetrazoles. Most
of the catalysts previously used have disadvantages, for example difﬁcult separation
of the reaction mixture, complicated synthetic methods, or use of polluting metals as
G. Qi (&) Á W. Zhang Á Y. Dai
Department of Chemistry and Biology, Yancheng Institute of Technology, Yancheng 224051, China
Res Chem Intermed (2015) 41:1149–1155