Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to 
Photocatalysis for Alkynylation Reactions

Amos, Stephanie G. E.; Cavalli, Diana; Le Vaillant, Franck; Waser, Jerome

doi:10.1002/anie.202110257

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Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions

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Le Vaillant, Franck
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Amos, S. G. E., Cavalli, D., Le Vaillant, F., & Waser, J. (2021). Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions. Angewandte Chemie International Edition, 60(44), 23827-23834. doi:10.1002/anie.202110257.

Cite as: https://hdl.handle.net/21.11116/0000-0009-66FF-6

Abstract

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C−H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.