Issue 13, 2024

Nitrogen-directed unactivated γ-C(sp3)–H functionalization of amides toward 7-membered lactones via photoredox catalysis

Abstract

Lactone motifs are prevalent in both naturally and synthetically bioactive molecules. We report herein a photoredox-catalyzed formal [5 + 2] annulation of O-acylhydroxamide derivatives with 1,3-dienes/1,3-enynes for the rapid synthesis of structurally diverse alkene/alkyne-containing 7-membered lactones. The reaction features selective transformation of distal unactivated C(sp3)–H bonds and a good substrate scope. A radical mechanism involving nitrogen-directed 1,5-hydrogen atom transfer (HAT) and facile coupling of alkyl radicals with 1,3-dienes/1,3-enynes, leading to the construction of 7-membered lactone motifs via C–O bond formation is proposed.

Graphical abstract: Nitrogen-directed unactivated γ-C(sp3)–H functionalization of amides toward 7-membered lactones via photoredox catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
29 Mar 2024
Accepted
16 May 2024
First published
18 May 2024

Org. Chem. Front., 2024,11, 3724-3728

Nitrogen-directed unactivated γ-C(sp3)–H functionalization of amides toward 7-membered lactones via photoredox catalysis

G. Tan, K. Xu, H. Qin and F. Liu, Org. Chem. Front., 2024, 11, 3724 DOI: 10.1039/D4QO00564C

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