Synfacts 2008(3): 0325-0325  
DOI: 10.1055/s-2008-1042666
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Hartwig-Buchwald Amination on Solid Supports

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
V. Zimmermann, S. Bräse*
Universität Karlsruhe, Germany
Further Information

Publication History

Publication Date:
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).