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Synthesis 2011(22): 3730-3740
DOI: 10.1055/s-0030-1260238
DOI: 10.1055/s-0030-1260238
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium(II) Acetate as Catalyst for the N-Alkylation of Aromatic Amines, Sulfonamides, and Related Nitrogenated Compounds with Alcohols by a Hydrogen Autotransfer Process
Further Information
Received
29 July 2011
Publication Date:
23 September 2011 (online)
Publication History
Publication Date:
23 September 2011 (online)
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
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