4.5 Review

Remote C-H Functionalization of 8-Aminoquinolinamides

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue 7, Pages 1270-1297

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201800276

Keywords

8-aminoquinoline; C5 functionalization; remote C-H functionalization; selectivity; single electron transfer mechanism

Funding

  1. UGC, New Delhi
  2. CSIR, New Delhi

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8-Aminoquinoline, a common structural motif present in many natural products, pharmaceuticals, agrochemicals, and important drugs has always been an attractive scaffold in synthetic organic chemistry. Recent years have witnessed the development of 8-aminoquinoline as a ligand in transition-metal-catalyzed C-H functionalizations. Therefore, synthesis of functionalized 8-aminoquinolines is of great importance and rapid generation of functionalized quinolines could be achieved by direct C-H functionalization. In this regard, since the seminal report of distal C5-H halogenations of quinoline, diverse C-X bond formation reactions have been published. This review is focused on the C5-H functionalization of 8-aminoquinolinamide derivatives, including not only C-C bond formation reactions but also carbon-heteroatom bond formations such as C-X (X=F, Cl, Br, I) C-S, C-Se, C-N, C-O, and C-P. In most cases, the C5 position is activated by a single electron transfer method employing either metal catalysts, photocatalysts, or metal-free conditions.

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