Palladium(II) Acetate as Catalyst
for the N-Alkylation of Aromatic Amines, Sulfonamides, and Related
Nitrogenated Compounds with Alcohols by a Hydrogen Autotransfer
Process

Ana Martínez-Asencio; Miguel Yus; Diego J. Ramón

doi:10.1055/s-0030-1260238

PAPER

Palladium(II) Acetate as Catalyst for the N-Alkylation of Aromatic Amines, Sulfonamides, and Related Nitrogenated Compounds with Alcohols by a Hydrogen Autotransfer Process

Ana Martínez-Asencio, Miguel Yus, Diego J. Ramón*
Departamento de Química Orgánica and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Fax: +34(96)5903549; e-Mail: djramon@ua.es;

Abstract

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Abstract

Palladium(II) acetate is a versatile, inexpensive, and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, sulfonamides, and phosphazenes, using, in all cases, primary alcohols as the initial source of the electrophile, through a hydrogen autotransfer process. The regioselectivity of the benzothiazol-2-amine alkylation is contrary to that found using halogenated electrophiles.

Key words

alcohols - alkylation - amines - hydrogen transfer - palladium

Full Text

References

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