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Preparation and Reactions of Indoleninyl Halides: Scaffolds for the Synthesis of Spirocyclic Indole Derivatives

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JournalOrganic Letters
DateAccepted/In press - 9 Nov 2016
DateE-pub ahead of print - 28 Nov 2016
DatePublished (current) - 16 Dec 2016
Issue number24
Volume18
Number of pages4
Pages (from-to)6328-6331
Early online date28/11/16
Original languageEnglish

Abstract

The dearomatization of 2-haloindole precursors allows access to indoleninyl halides, a hitherto underexploited functional handle with broad synthetic utility. Indoleninyl iodides have been shown to react via three distinct modes: hydrolysis, nucleophilic substitution, and cross-coupling. This allows a broad array of functionalized spirocyclic indole derivatives to be generated from a common starting material. They are also useful precursors to functionalized quinolines following migratory rearrangement and subsequent derivatization reactions.

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© 2016 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

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