Arcadi A,
Cacchi S,
*,
Marinelli F.
Sapienza University of Rome, Italy
A Versatile Approach to 2,3-Disubstituted Indoles through the Palladium-Catalysed
Cyclization of o-Alkynyltrifluoroacetanilides with Vinyl Triflates and Aryl Halides.
Tetrahedron Lett. 1992;
33: 3915-2918
DOI:
10.1016/S0040-4039(00)74818-0
Key words
palladium catalysis - indoles - Cacchi reaction - nucleopalladation
Significance
Cacchi and co-workers report a palladium-catalyzed synthesis of disubstituted indoles.
This approach utilizes aryl halides and vinyl triflates with alkyne-tethered aryl
nucleophiles to synthesized highly decorated indoles. The reaction is suitable for
a wide range of functionalities and has now been extended to diverse scaffolds.
Comment
The reaction proceeds via an initial oxidative addition of the electrophile. Subsequent
coordination, nucleopalladation and reductive elimination yield the product. The scaffolds
arising from this reaction have shown biological activity.
