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

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 lact...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 11; no. 13; pp. 3724 - 3728
Main Authors Tan, Guang-Qiang, Xu, Ke-Dong, Qin, Hai-Tao, Liu, Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.06.2024
Royal Society of Chemistry
Subjects
Alkynes
Amides
Catalysis
Chemical reactions
Chemistry
Chemistry, Organic
Dienes
Hydrogen atoms
Lactones
Nitrogen
Photoredox catalysis
Physical Sciences
Science & Technology
Substrates
CYCLIZATION
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Summary: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(sp(3))-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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d4qo00564c