Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2021; 17(03): 0307
DOI: 10.1055/s-0040-1720310
DOI: 10.1055/s-0040-1720310
Metals in Synthesis
Larock Indole Synthesis
Larock RC,
*,
Yum EK,
Refvik MD.
Iowa State University, USA
Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes.
J. Org. Chem. 1998;
63: 7652-7662
DOI: 10.1021/jo9803277.
Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes.
J. Org. Chem. 1998;
63: 7652-7662
DOI: 10.1021/jo9803277.
Key words
Larock indole synthesis - palladium catalysis - annulation - regioselectivity - alkyne insertion
Significance
In 1998, Larock and co-workers reported a palladium-catalyzed coupling of 2-iodoanilines with internal alkynes to afford 2,3-disubstituted indoles; an important heterocyclic scaffold. The reaction proceeds under mild conditions to afford the indole products in good to excellent yields.
#
Comment
The regioselectivity of the reaction is dependent on both substrate and reaction conditions employed. When more than one equivalent of the chloride is added, the reaction rate is retarded, and there is an increase in the formation of side products.
#
Review
R. Chinchilla, C. Nájera Chem. Rev. 2014, 114, 1783−1826.
#
#
Publication History
Article published online:
16 February 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany