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Hartwig-Buchwald Amination on Solid Supports
V. Zimmermann, S. Bräse*
Universität Karlsruhe, Germany
21 February 2008 (online)
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).