Hartwig-Buchwald Amination on Solid Supports

Significance

The solid-phase synthesis of N-substituted benzotriazoles via the Hartwig-Buchwald reaction was reported. Thus, the ortho-halo and ortho-aminoarene triazene resins 1, 2, and 4 were prepared from aryl diazonium salts and benzylaminomethyl polystyrene. The Hartwig-Buchwald reactions of 1 with amines, and 4 with haloarenes were carried out with a Pd catalyst to give the corresponding triazene-linked N-substituted 2-anilines 5. 1H-Benzotriazoles 6 were obtained under mild acidic conditions via ortho-aminoarene diazonium salts (36 examples; 1-88% yield, 60-99% purity).