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

Agnieszka Październiok-Holewa, Jakub Adamek, R. Mazurkiewicz, K. Zielińska
Published 2013 · Chemistry

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Abstract Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr)2EtN 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)2EtN in a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as new, convenient and effective α-amidoalkylation agents. GRAPHICAL ABSTRACT
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