tBu4NCl/K2S2O8 System Induced C-2 Functionalization of 8-Aminoquinoline Amides with Primary Alcohols |
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| Authors: | Kaixin Zhang Jianxiong Xu Jinxiang Xiao Prof. Ronglin Zhong Prof. Jizhen Li |
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| Affiliation: | 1. Department of Organic Chemistry, College of Chemistry, Jilin University, 2519 Jiefang Road, 130021 Changchun, P. R. China;2. Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, College of Chemistry, Jilin University, 130021 Changchun, P. R. China |
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| Abstract: | A metal and light-free Minisci-type acylation approach of 8-aminoquinoline amides with general primary alcohols was demonstrated under tBu4NCl/K2S2O8 system. Simultaneously, the C2−H alkylation can be realized by accident for special benzyl alcohols bearing strong electron-donating groups. Most N-heterocycles were also compatible to afford corresponding acylated products. Furthermore, the mechanism investigation reveals that chlorine radical induced the original ketyl radical generation through abstracting the α-C−H from the alcohols, then underwent nucleophilic carbon-centered radicals addition, deprotonation, and oxidation to provide the target acylation products. |
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| Keywords: | acylation and alkylation alcohols 8-aminoquinolines chlorine radical Minisci reaction |
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