Tetrabutylammonium fluoride (TBAF) is an efficient catalyst in the [3 + 2] cycloaddition reaction of organic nitriles 1 with trimethylsilyl azide (TMSN(3)) in solventless conditions. The corresponding 5-substituted 1H-tetrazoles 2 were obtained under mild conditions and in 80-97% yields.

Tetrazole derivativesTetrazole derivatives R 0310 TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under SolventlessConditions. -The [3 + 2] cycloaddition of nitriles (I) with Tms-N 3 is efficiently catalyzed by Bu 4 NF under solventless conditions. A wide range of nitriles is tolerated, including (het)aromatic and aliphatic nitriles with varying substituents and even sterically demanding nitriles. The use of anionic catalysis is especially favorable in the case of acid-labile substrates. -(AMANTINI*, D.; BELEGGIA, R.; FRINGUELLI, F.; PIZZO, F.; VACCARO, L.; J.