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Synfacts 2024; 20(11): 1180
DOI: 10.1055/s-0043-1775172
Metals in Synthesis

Synthesis of 2,3-Disubstituted Indoles via Palladium Catalysis

Contributor(s):
Mark Lautens
,
Ramon Arora
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
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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.


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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.


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Publication History

Article published online:
16 October 2024

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