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Synfacts 2021; 17(03): 0307
DOI: 10.1055/s-0040-1720310
Metals in Synthesis

Larock Indole Synthesis

Contributor(s):
Mark Lautens
,
Randy Sanichar
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
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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.


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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.


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Review

R. Chinchilla, C. Nájera Chem. Rev. 2014, 114, 1783−1826.


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Publication History

Article published online:
16 February 2021

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