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Electron-deficient nitrogen-containing heteroaromatics, such as quinoline, isoquinoline, and pyridine, were treated with benzoyl peroxide in dioxane, tetrahydropyran, tetrahydrofuran, diethyl ether, and dipropyl ether at 80C to form alkylated nitrogen-containing heteroaromatics in good yields under transition-metal-free conditions. This method was successfully applied to the preparation of lariat aza-crown ethers using 18-crown-6 or 15-crown-5 with quinoline and isoquinoline in the presence of benzoyl peroxide in good yields under irradiation conditions with a Hg lamp.
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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis