10.1002/ejoc.202000289
European Journal of Organic Chemistry
FULL PAPER
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heteroarenes with cyclopropanols under metal−, acid−, and
photocatalyst−free conditions. Avoiding the involvement of
metallic reagents is impressive since it avoids metal toxicity and
minimizes environmental pollution. The acid− and photocatalyst
free conditions make the reaction more compatible with acid− or
light−senstive
substrates.
In
addition,
The
resulting
β−heteroarylated ketones are also the feedstock for the
construction of many biologically active molecules including
natural alkaloids and pharmaceutical agents.[18,19] The
environmental friendliness together with the scale−up
experiments make the protocol attractive and practical in
synthetic applications.
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Experimental Section
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for
β−carbonyl
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reaction tube
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a
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(1, 0.3 mmol), cyclopropanol (2, 2.0 equiv.), K2S2O8 (4.0 equiv.)
and DMSO/H2O (4:1, 5.0 mL) successively. The mixture was
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Na2SO4. Removal of the solvent afforded the crude product,
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The radical scavenger experiment: Under N2 atmosphere, a
reaction tube equipped with a magnetic stir bar was charged
with heteroarene (1, 0.3 mmol), cyclopropanol (2, 2.0 equiv.),
K2S2O8 (4.0 equiv.), DMSO/H2O (4:1, 5.0 mL) and TEMPO (3.0
equiv.) successively. The mixture was allowed to react at 70 °C
for 12 h. Then the mixture was charged in 50 mL water,
neutralized by Na2CO3 (1 M) to pH 7 and extracted with CH2Cl2
(20 mL x 3 times). The CH2Cl2 layers were combined, dried over
Na2SO4 and analyzed by TLC and GC−MS.
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This work was financially supported by Science Foundation for
Distinguished Scholars of Dongguan University of Technology
(Nos. 196100041 and 196100041051), Postdoctor Foundation of
Dongguan University of Technology (No. 196100040006),
National Natural Science Foundation of China (No. 51773165
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Conflict of interest
The authors declare no conflict of interest.
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Keywords: C−H alkylation • heteroarenes • cyclopropanol
•β−heteroarylated ketones • ring−opening
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