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Synfacts 2025; 21(07): 709
DOI: 10.1055/a-2601-4975
Metals in Synthesis

Palladium-Catalyzed Synthesis of 2,3-Dialkylindoles from ortho-Alkenylisocyanobenzenes

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Dáiríne M. Morgan 
Cheng S, Liang Y, Zhang T, Chen M, Li J, Zhang X, Luo S *, Zhu Q *. Guangzhou Institutes of Biomedicine and Health, P. R. China
Regiospecific 2,3-Dialkylindole Synthesis Enabled by Alkylpalladium 1,2-Migration to In Situ Formed Aldimine.

Angew. Chem. Int. Ed. 2025;
DOI: 10.1002/anie.202501582
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Keywords

[1,2]-alkylpalladium migration - aldimines - indoles - palladium catalysis

Significance

A palladium-catalyzed protocol for the synthesis of 2,3-dialkylindoles starting from ortho-alkenylisocyanobenzenes is reported. The catalytic cycle involves a 1,2-migratory addition of an alkylpalladium to an aldiminium intermediate as the key step.


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Comment

13C-Labelled isocyanide furnished the indole 13C-labeled at the C2 position, which confirmed that the isocyano carbon is the origin of the C2 indole atom. This result, along with DFT calculations and deuterium-labelling experiments, support the proposed reaction mechanism.


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Publication History

Article published online:
23 June 2025

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