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Synfacts 2005(0): 0079-0079  
DOI: 10.1055/s-2005-869890
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymer-Supported Organotin Reagents for Regioselective Halogenation of Aromatic Amines

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Naoshi Fukuyama
J.-M. Chrétien, F. Zammattio*, E. Le Grognec, M. Paris, B. Cahingt, G. Montavon, J.-P. Quintard*
Université de Nantes, France
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Publikationsdatum:
20. Juli 2005 (online)

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Significance

Nine N-triorganostannylamines were prepared from aromatic amines and polymer-supported tributyltin iodide. They reacted with bromine or iodine monochloride to give para-halogenated aromatic amines in 41-76% yields with polymeric tin halides. Excellent para regio­selectivity was achieved in the case of iodination (para/ortho >99/1). The resulting polymer-supported tin halides were reusable for five times.