Regioselective Direct C-H Bond Heteroarylation of Thiazoles Enabled by an Iminopyridine-Based α-Diimine Nickel(II) Complex Evaluated by DFT Studies.

Autor: Arche PDE; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Chatterjee S; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Talukder MM; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Miller JT; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Cue JMO; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Udamulle Gedara CM; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Lord RL; Department of Chemistry, Grand Valley State University, Allendale, Michigan 49401, United States., Biewer MC; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States., Cisneros GA; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States.; Department of Physics, University of Texas at Dallas, Richardson, Texas 75080, United States., Stefan MC; Department of Chemistry and Biochemistry, University of Texas at Dallas, Richardson, Texas 75080, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Sep 01; Vol. 88 (17), pp. 12319-12328. Date of Electronic Publication: 2023 Aug 21.
DOI: 10.1021/acs.joc.3c01021
Abstrakt: Direct C-H bond arylation is a highly effective method for synthesizing arylated heteroaromatics. This method reduces the number of 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 a 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 revealed that the mechanism of C-H activation in 4-methylthiazole involves an electrophilic aromatic substitution.
Databáze: MEDLINE
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