Base-Catalyzed [3 + 2] Cycloaddition of N-Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2H-Pyrroles via Intermediate Pyrrolines
Ivan A. Bidusenko, Elena Yu. Schmidt, Igor A. Ushakov, Alexander V. Vashchenko and Boris A. Trofimov*
*A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia,
Email: boris_trofimov
irioch.irk.ru
I. A. Bidusenko, E. Y. Schmidt, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov, Org. Lett., 2021, 23, 4121-4126.
DOI: 10.1021/acs.orglett.1c01009
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Abstract
N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in KOtBu/DMSO solution to provide 2,3,5-triarylpyrrolines in good yields. A subsequent in situ oxidation with chloranil or DDQ gives 2,3,5-triaryl-2H-pyrroles in good yields.
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proposed mechanism
Key Words
ID: J54-Y2021
