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tBu4NCl/K2S2O8 System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

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A metal and light-free Minisci-type C2−H functionalization approach including acylation and alkylation of 8-aminoquinoline amides with general primary alcohols was demonstrated under tBu4NCl/K2S2O8 system. The chlorine radical induced the original ketyl radical generation from alcohols, and the mechanism for the acylation reaction was investigated in detail.


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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