4.7 Article

Palladium-catalyzed intramolecular diastereoselective dearomatization reaction of indoles with N-tosylhydrazones

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ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 20, 页码 5895-5901

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00893e

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  1. National Natural Science Foundation of China [21776056]
  2. Natural Foundation of Hebei Province (CN) [B2020202010, ZD2021026]

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This study has successfully developed a novel dearomative reaction method for the synthesis of structurally diverse tetracyclic indolines through a series of reaction steps. The reaction exhibits high yields, excellent diastereoselectivities, and good compatibility with functional groups.
A novel, highly diastereoselective palladium-catalyzed dearomative reaction of N-halobenzoyl o-haloaniline derivatives has been developed using functionalized N-tosylhydrazones as the coupling partners. This cascade dearomative protocol, which proceeds through sequential dearomative carbopalladation, migratory insertion, and beta-hydride elimination, provides a reliable and straightforward access to a wide range of structurally diverse tetracyclic indolines with C2-quaternary stereocenters in moderate to good yields and excellent diastereoselectivities with good functional group compatibility.

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