Metal-Free Regioselective N 2 -Arylation of 1 H -Tetrazoles with Diaryliodonium Salts.

We describe a simple, metal-free regioselective N 2 -arylation strategy for 5-substituted-1 H -tetrazoles with diaryliodonium salts to access 2-aryl-5-substituted-tetrazoles. Diaryliodonium salts with a wide range of both electron-rich and previously challenged electron-deficient aryl groups are applicable in this method. Diversely functionalized tetrazoles are tolerable also. We have devised a one-pot system to synthesize 2,5-diaryl-tetrazoles directly from nitriles. The synthetic utility of this method is furthered extended to late-stage arylation of two biologically active molecules.