Issue 52, 2024

Catalytic tert-alkylation of enamides via C–C bond cleavage under photoredox conditions

Abstract

Efficient C–C bond cleavage is recognized as a persistent challenge in the field of synthetic methodology. In this study, we found that tertiary alkyl radicals are smoothly formed from tertiary alkylated dienones (BHT adducts) via SET, using PDI as a photocatalyst. Resulting tert-alkyl radicals could be applied to the tert-alkylation of enamides. The driving force of this C–C bond cleavage reaction is the mesolytic cleavage of the BHT adducts. The mechanistic study revealed that PDI anion radical is the key active species during the catalytic cycle.

Graphical abstract: Catalytic tert-alkylation of enamides via C–C bond cleavage under photoredox conditions

Supplementary files

Article information

Article type
Communication
Submitted
09 Apr 2024
Accepted
28 May 2024
First published
28 May 2024

Chem. Commun., 2024,60, 6623-6626

Catalytic tert-alkylation of enamides via C–C bond cleavage under photoredox conditions

N. Tsuchiya, A. Oku and T. Nishikata, Chem. Commun., 2024, 60, 6623 DOI: 10.1039/D4CC01643B

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