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DOI: 10.1055/s-0042-1752608
Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Cyclization of ortho-Alkynyl Anilines
A Versatile Approach to 2,3-Disubstituted Indoles through the Palladium-Catalyzed Cyclisation of o-Alkynyltrifluoro-acetanilides with Vinyl Triflates and Aryl Halides.
Tetrahedron Lett. 1992;
33: 3915-3918
DOI: 10.1016/s0040-4039(00)74818-0
Significance
Indoles are structural motifs found in a wide variety of natural products and pharmaceutical agents. While other palladium-catalyzed indole syntheses had been primarily focused on the cyclization of compounds containing pre-installed substituents of the desired indole, Cacchi and co-workers demonstrated a modular synthesis of 2,3-disubstituted indoles using a variety of 2-alkynyl anilines and aryl halides or vinyl triflates, streamlining the synthesis of this class of compound.
Comment
The authors note that other bases such as triethylamine performed poorly compared to potassium carbonate. Similarly, indole products were not observed when employing aniline derivatives with a free amino group or acetamido group, highlighting the importance for a stronger electron-withdrawing group to be present on the nitrogen atom.
Publikationsverlauf
Artikel online veröffentlicht:
16. Juni 2023
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