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Palladium-Catalyzed (3 + 2) Annulation of Aromatic Acids by C(sp<sup>3</sup>)–H Olefination and Decarboxylative Cross-Coupling Reaction

Xiaobo Xu, Yangyang Wang, Xiao Yu, Xian Liu, Liqiang Hao, Yafei Ji

2024Organic Letters16 citationsDOI

Abstract

A palladium-catalyzed (3 + 2) annulation of 2-methylbenzoic acid with maleimide using Ac-Leu-OH as a powerful ligand has been reported. Through a site-selective γ-C(sp 3 )–H olefination reaction and a sequential decarboxylative cross-coupling reaction, a five-membered cyclic ring was obtained as the final product. This novel reaction features great site selectivity and reactivity to generate various cyclic products in moderate to good yields.

Topics & Concepts

AnnulationChemistryPalladiumCatalysisRing (chemistry)Coupling reactionMedicinal chemistryReactivity (psychology)Ligand (biochemistry)SelectivityMaleimideCombinatorial chemistryOrganic chemistryBiochemistryPathologyReceptorMedicineAlternative medicineCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions
Palladium-Catalyzed (3 + 2) Annulation of Aromatic Acids by C(sp<sup>3</sup>)–H Olefination and Decarboxylative Cross-Coupling Reaction | Litcius