Synthesis of 2,2,5-Trisubstituted 2H‑Pyrroles and 2,3,5-Trisubstituted 1H‑Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-aryl...

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Veröffentlicht in:Organic letters 2019-09, Vol.21 (17), p.6972-6977
Hauptverfasser: Yamaguchi, Miyuki, Fujiwara, Sakiko, Manabe, Kei
Format: Artikel
Sprache:eng
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Zusammenfassung:Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02559