Copper-Catalyzed Remote C–H Functionalizations of Naphthylamides through a Coordinating Activation Strategy and Single-Electron-Transfer (SET) Mechanism

Achieving p-CAr–H site selectivity is one of the major challenges in direct carbon–hydrogen (C–H) functionalization reactions. Herein, the copper-catalyzed and picolinamide-assisted remote p-C–H sulfonylation of 1-naphthylamides was realized. The synthetic utility of this method was further examined...

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Published inACS catalysis Vol. 7; no. 4; pp. 2661 - 2667
Main Authors Li, Jun-Ming, Wang, Yong-Heng, Yu, Yang, Wu, Rui-Bo, Weng, Jiang, Lu, Gui
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.04.2017
Subjects
regioselectivity
radical reactions
copper
C−H activation
naphthalene
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Summary:Achieving p-CAr–H site selectivity is one of the major challenges in direct carbon–hydrogen (C–H) functionalization reactions. Herein, the copper-catalyzed and picolinamide-assisted remote p-C–H sulfonylation of 1-naphthylamides was realized. The synthetic utility of this method was further examined by sequential functionalizations and the efficient synthesis of the pharmaceutically useful 5-HT6 serotonin receptor ligand. This approach also provided a general strategy for other p-C–H bond functionalization, such as highly selective constructions of C–O, C–Br, C–I, C–C, and C–N bonds. Control experiments and theoretical calculations suggested that this C–H sulfonylation reaction might proceed through a single-electron-transfer process.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b03671