Polymer-Supported Organotin Reagents for Regioselective Halogenation of Aromatic Amines

doi:10.1055/s-2005-869890

Synfacts 2005(0): 0079-0079
DOI: 10.1055/s-2005-869890

Polymer-Supported Synthesis

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
Polymer-Supported Organotin Reagents for Regioselective Halogenation of Aromatic Amines
J. Org. Chem. 2005, 70: 2870-2873

Abstract

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Key words

halogenation - aromatic amines - organotin halides

Significance

<P>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. </P>

Comment

<P>The reaction system contains two advantages: (1) halogenation using a triorganotin halide does not generate a hydrohalic acid, and (2) the polymer-supported method decreases the organotin residue in the products.</P>

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