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tBu4NCl/K2S2O8 System Induced C-2 Functionalization of 8-Aminoquinoline Amides with Primary Alcohols
Authors:Kaixin Zhang  Jianxiong Xu  Jinxiang Xiao  Prof. Ronglin Zhong  Prof. Jizhen Li
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
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.
Keywords:acylation and alkylation  alcohols  8-aminoquinolines  chlorine radical  Minisci reaction
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