Issue 1, 2023

Palladium-catalyzed intramolecular C–H amination using aluminum nitrate as the oxidant

Abstract

A palladium catalyzed intramolecular C(sp2)–H amination using a readily available aluminum nitrate (Al(NO3)3·9H2O) as the oxidant is reported. The C–H amination is promoted by in situ nitration of the quinoline directing group (DG). The oxindole products can be efficiently converted into novel polycyclic compounds (up to 7 fused rings) via a sequential reduction/cyclization involving the DG. Mechanistic studies indicate that nitration of the quinoline DG favors the following activation of γ-aryl C(sp2)–H bonds over β-methyl C(sp3)–H bonds.

Graphical abstract: Palladium-catalyzed intramolecular C–H amination using aluminum nitrate as the oxidant

Supplementary files

Article information

Article type
Research Article
Submitted
05 Oct 2022
Accepted
12 Nov 2022
First published
15 Nov 2022

Org. Chem. Front., 2023,10, 109-114

Palladium-catalyzed intramolecular C–H amination using aluminum nitrate as the oxidant

K. Jia, Y. Xue, D. Tu, J. Luo and C. Jiang, Org. Chem. Front., 2023, 10, 109 DOI: 10.1039/D2QO01562E

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