Photocatalytic Spirocyclization of 2-Alk-ω-enyl-Substituted Cycloalkane-1,3-diones

Abstract

When irradiated with visible light, various cyclic 2-alk-4-enyl-substituted 1,3-diketones undergo an intramolecular endo-addition (m = 1) onto the double bond resulting in spirocyclic products (11 examples, 62–92% yield). Both an organic (TXT: thioxanthone, 20 mol%) and an organometallic Ir-based photocatalyst (5 mol%) promote the reaction. Addition of triisopropylthiophenol is required to secure high yields. The spirocyclization of a 2-alk-5-enyl-substituted substrate (m = 2) delivers a mixture of the seven-membered endo- and the six-membered exo-cyclization products.

Key words

catalysis - cyclization - electron transfer - iridium - photochemistry - radical reaction

Publication History

Received: 28 November 2022

Accepted after revision: 28 December 2022

Accepted Manuscript online:
28 December 2022

Article published online:
30 January 2023

• References and Notes

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