Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer.

Autor: Puleo TR; Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States., Klaus DR; Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States., Bandar JS; Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2021 Aug 18; Vol. 143 (32), pp. 12480-12486. Date of Electronic Publication: 2021 Aug 04.
DOI: 10.1021/jacs.1c06481
Abstrakt: We report a general protocol for the direct C-H etherification of N -heteroarenes. Potassium tert -butoxide catalyzes halogen transfer from 2-halothiophenes to N -heteroarenes to form N -heteroaryl halide intermediates that undergo tandem base-promoted alcohol substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcohols with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions.
Databáze: MEDLINE