C–N Cross-Coupling via Photoexcitation of Nickel–Amine Complexes
Department of Chemistry, Colorado State University , Fort Collins , Colorado 80523 , United States
J. Am. Chem. Soc., Article ASAP
DOI: 10.1021/jacs.8b03744
Publication Date (Web): May 22, 2018
Copyright © 2018 American Chemical Society
Cite this:J. Am. Chem. Soc. XXXX, XXX, XXX-XXX
Abstract
C–N cross-coupling is an important class of reactions with far-reaching impacts across chemistry, materials science, biology, and medicine. Transition metal complexes can elegantly orchestrate diverse aminations but typically require demanding reaction conditions, precious metal catalysts, or oxygen-sensitive procedures. Here, we introduce a mild nickel-catalyzed C–N cross-coupling methodology that operates at room temperature using an inexpensive nickel source (NiBr2·3H2O), is oxygen tolerant, and proceeds through direct irradiation of the nickel–amine complex. This operationally robust process was employed for the synthesis of diverse C–N-coupled products (40 examples) by irradiating a solution containing an amine, an aryl halide, and a catalytic amount of NiBr2·3H2O with a commercially available 365 nm LED at room temperature without added photoredox catalyst and the amine substrate serving additional roles as the ligands and base. Density functional theory calculations and kinetic isotope effect experiments were performed to elucidate the observed C–N cross-coupling reactivity.
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b03744.
General information; Figures S1–S25 and Tables S1 and S2, detailing reaction development and optimization, photoreactor development, UV–visible spectroscopy, fluorimetry, kinetic isotope effect, computational details, and characterizations; NMR spectra; and coordinates of molecular structures (PDF)
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