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Synfacts 2024; 20(01): 0057
DOI: 10.1055/s-0043-1772926
Metals in Synthesis

Hegedus Indole Synthesis: Intramolecular Nucleopalladation of ortho-Allyl Aryl Nucleophiles

Contributor(s):
Mark Lautens
,
Jonathan Bajohr
Hegedus LS, *, Allen GF, Waterman EL. Colorado State University, USA
Palladium Assisted Intramolecular Amination of Olefins. A New Synthesis of Indoles.

J. Am. Chem. Soc. 1976;
98: 2674-2676
DOI: 10.1021/ja00425a051.
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Key words

indoles - aminopalladation - palladium

Significance

Indoles are widely found within natural products, derivatives of which are commonly used as therapeutic agents for a broad range of indications. Hegedus and co-workers report an efficient synthesis of indoles (and other) heterocycles from the cyclization of aryl nucleophiles bearing an ortho-allyl group. The aminopalladation chemistry of Hegedus has been employed in the synthesis of ergot alkaloids and has inspired additional nucleo­palladation methodologies to be developed.


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Comment

Although the yields are not document­ed in detail, the scope of this aminopalladation was established towards heterocycles including to carb­azole, indoline, dihydroquinoline, tetrahydroisoquinoline, and isocoumarin derivatives. Hegedus and co-workers published a follow-up report in 1978, outlining a catalytic methodology to perform the same reaction, employing benzoquinone as an oxidant to regenerate the necessary Pd(II) catalyst.


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Publication History

Article published online:
08 December 2023

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