Metal-free site-selective C–H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with azobisisobutyronitrile |
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Authors: | Mengfei Zhao Zengxin Qin Kaixin Zhang Jizhen Li |
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Affiliation: | Department of Organic Chemistry, College of Chemistry, Jilin University, 2519 Jiefang Road, Changchun 130021 P. R. China, |
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Abstract: | Using K2S2O8, an efficient and metal-free site-selective C–H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with AIBN (azobisisobutyronitrile) was developed. Without any catalyst, various substrates and functional groups were compatible to afford corresponding products in moderate to high yields. A mechanism study displayed that a radical–radical coupling process was involved via the N-centered radical generation and delocalization of aryl amides.An efficient metal-free cyanoalkylation of 8-aminoquinoline and aniline-derived amides was achieved in the presence of K2S2O8. The method showed good substrate tolerance and also suitable for bromination and dimerization reactions. |
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