Amidoalkylating Properties of 1-(N-Acylamino)Alkyltriphenylphosphonium Salts

Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr) 2 EtN to give the expected α-amidoalkylation products, usually in good or very good yields. α-Amidoalkylation of dialkyl malonates or ac...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2013-01, Vol.188 (1-3), p.205-212
Main Authors: Październiok-Holewa, Agnieszka, Adamek, Jakub, Mazurkiewicz, Roman, Zielińska, Katarzyna
Format: Article
Language:English
Subjects:
1-(N-acylamino)alkyltriphenylphosphonium salts
enamines
nucleophilic substitution
α-Amidoalkylation
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Summary:Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr) 2 EtN to give the expected α-amidoalkylation products, usually in good or very good yields. α-Amidoalkylation of dialkyl malonates or acetylacetates requires the application of a much stronger base (DBU) and gives the best results under the influence of microwave irradiation. α-Amidoalkylation of enamines was carried out successfully in the presence of (i-Pr) 2 EtN in a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as new, convenient and effective α-amidoalkylation agents.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2012.744014