Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 12, Pages 8381-8388Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00793
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Funding
- National Natural Science Foundation of China [21971079, 21971080, 21772051]
- 111 Project [B17019]
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A novel I-2-mediated Povarov reaction has been developed for the synthesis of 2,4-substituted quinolines using arylacetylenes and anilines. The arylacetylene serves as both a diene precursor and dienophile in this reaction. Preliminary mechanistic studies suggest that the I-2/DMSO system enables the oxidative carbonylation of C(sp)-H of arylacetylene followed by a [4 + 2] cycloaddition reaction.
A novel I-2-mediated Povarov reaction of arylacetylenes and anilines for the synthesis of 2,4-substituted quinolines has been developed, in which arylacetylene first acts as both a diene precursor and dienophile. This work further develops the Povarov reaction to expand the types of diene precursors. Preliminary mechanistic studies indicate that the I-2/DMSO system realized the oxidative carbonylation of C(sp)-H of arylacetylene and then undergoes a [4 + 2] cycloaddition reaction.
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