A New Synthesis of Benzoazacrown Ethers Through Pd-Catalyzed Intramolecular Cycloamination Reactions

Rafik Omar-Amrani; Raphael Schneider; Yves Fort

doi:10.2174/157017807781212058

Abstract

A new synthesis of twelve-, fifteen-, and eighteen-membered benzoazacrown ethers using palladium-catalyzed intramolecular amination is reported. Couplings proceeded in good yields using an in situ generated Pd(0) catalyst associated to N,N-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as ligand and t-BuONa as the base.

Keywords: Intramolecular aryl amination, Pd(0) catalyst, N-heterocyclic carbene, benzoazacrown ethers

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Letters in Organic Chemistry

Title: A New Synthesis of Benzoazacrown Ethers Through Pd-Catalyzed Intramolecular Cycloamination Reactions

Volume: 4 Issue: 5

Author(s): Rafik Omar-Amrani, Raphael Schneider and Yves Fort

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Keywords: Intramolecular aryl amination, Pd(0) catalyst, N-heterocyclic carbene, benzoazacrown ethers

Abstract: A new synthesis of twelve-, fifteen-, and eighteen-membered benzoazacrown ethers using palladium-catalyzed intramolecular amination is reported. Couplings proceeded in good yields using an in situ generated Pd(0) catalyst associated to N,N-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as ligand and t-BuONa as the base.

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Rafik Omar-Amrani , Raphael Schneider and Yves Fort , A New Synthesis of Benzoazacrown Ethers Through Pd-Catalyzed Intramolecular Cycloamination Reactions, Letters in Organic Chemistry 2007; 4 (5) . https://dx.doi.org/10.2174/157017807781212058