Issue 43, 2023

Copper complexes for the chemoselective N-arylation of arylamines and sulfanilamides via Chan–Evans–Lam cross-coupling

Abstract

Copper(II) complexes with tridentate NNN-ligands were utilized for Chan–Evans–Lam (CEL) cross-coupling reactions to enable the N-arylation of multifarious N-nucleophiles through the activation of aryl boronic acids. A condition-specific methodology was developed to chemoselectively target the amine versus sulfonamide N-arylation of 4-aminobenzenesulfonamide using new catalysts. Two different pyridine-based ligands and corresponding copper(II) complexes were characterized using 1H and 13C-NMR, FTIR, and UV-vis spectroscopy, HRMS, single-crystal X-ray diffraction, and cyclic voltammetry. Solvent and base-controlled cross-coupling reactions were observed, which led to the optimization of selective conditions for targeted C–N bond formation of sulfanilamides. Beyond the chemoselective processes reported here, a breadth of N-nucleophiles including sulfanilamides and arylamines were screened for arylation by this CEL catalyst.

Graphical abstract: Copper complexes for the chemoselective N-arylation of arylamines and sulfanilamides via Chan–Evans–Lam cross-coupling

Supplementary files

Article information

Article type
Paper
Submitted
16 Aug 2023
Accepted
26 Sep 2023
First published
04 Oct 2023

Dalton Trans., 2023,52, 15986-15994

Copper complexes for the chemoselective N-arylation of arylamines and sulfanilamides via Chan–Evans–Lam cross-coupling

S. Raju, M. Teimouri, B. Adhikari, B. Donnadieu, S. L. Stokes and J. P. Emerson, Dalton Trans., 2023, 52, 15986 DOI: 10.1039/D3DT02659K

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