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Visible-light-induced intramolecular charge transfer in the radical spirocyclisation of indole-tethered ynones

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JournalChemical Science
DateAccepted/In press - 12 Dec 2019
DateE-pub ahead of print - 13 Dec 2019
DatePublished (current) - 7 Feb 2020
Issue number5
Volume11
Number of pages8
Pages (from-to)1353-1360
Early online date13/12/19
Original languageEnglish

Abstract

Indole-tethered ynones form an intramolecular electron donor-acceptor complex that can undergo visible-light-induced charge transfer to promote thiyl radical generation from thiols. This initiates a novel radical chain sequence, based on dearomatising spirocyclisation with concomitant C-S bond formation. Sulfur-containing spirocycles are formed in high yields using this simple and mild synthetic protocol, in which neither transition metal catalysts nor photocatalysts are required. The proposed mechanism is supported by various mechanistic studies, and the unusual radical initiation mode represents only the second report of the use of an intramolecular electron donor-acceptor complex in synthesis.

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© The Royal Society of Chemistry 2020

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