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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 188, 2013 - Issue 1-3: 19th International Conference on Phosphorus Chemistry (ICPC-2012) Rotterdam, 8–12 July, 2012
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Original Articles

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

Agnieszka Październiok-Holewa Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, PL 44-100, Gliwice, Poland
,
Jakub Adamek Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, PL 44-100, Gliwice, Poland
,
Roman Mazurkiewicz Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, PL 44-100, Gliwice, Poland
&
Katarzyna Zielińska Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, PL 44-100, Gliwice, Poland
Pages 205-212 | Received 14 Sep 2012, Accepted 23 Oct 2012, Published online: 08 May 2013
 
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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

Acknowledgments

The financial help of the Ministry of Science and Higher Education of Poland (Grant No. N N204 165636) is gratefully acknowledged.

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