期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 32, 页码 12480-12486出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c06481
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资金
- National Institute of General Medical Sciences of the National Institutes of Health [R35GM138350]
- American Chemical Society Petroleum Research Fund [60171-DNI1]
A new method is reported for the direct C-H etherification of N-heteroarenes under basic conditions, using potassium tert-butoxide as a catalyst and 2-halothiophenes as a reagent for halogen transfer. This protocol allows for regioselective oxidative coupling of alcohols with a variety of N-heteroarenes, such as 1,3-azoles, pyridines, diazines, and polyazines.
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.
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