Regioselective Direct C−H Bond (Hetero)arylation of Thiazoles Enabled by a Novel Iminopyridine-Based α‐Diimine Nickel(II) Complex Evaluated by DFT Studies.

12 May 2023, Version 1

Abstract

Direct C−H bond arylation is a highly effective method for synthesizing arylated heteroaromatics. This method reduces synthetic steps and minimizes the formation of impurities. We report an air and moisture-stable iminopyridine-based α-diimine nickel (II) complex for direct C5-H bond arylation of thiazole derivatives. Under low catalyst loading and performing the reactions at lower temperatures (80 °C) under aerobic conditions, we produced mono- and diarylated thiazole units. Competition experiments and density functional theory calculations (DFT) revealed that the mechanism of C−H activation in 4-methylthiazole involves electrophilic aromatic substitution.

Keywords

C−H activation
thiazoles
Nickel
DFT
regioselectivity
mechanism

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
The supporting information has additional data about the characterization of N-(2-ethylphenyl)-1-(pyridin-2-yl)methanimines (NMR), the electronic structure of intermediates, Reaction energy profile for Ni0/NiII-catalysed mechanism, and xyz coordinates of the optimized geometries involved in Ni0/NiII mechanism and HOMO and Fukui analysis of 4-methylthiazole
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.