Article Dans Une Revue Angewandte Chemie International Edition Année : 2023

A Three‐Component Arene Difunctionalization: Merger of C(sp 3 )/(sp 2 )−H Bond Addition

Résumé

Abstract A tandem three‐component C−H bond addition involving the activation of an inert C(sp 3 )−H bond is reported. The process enables the direct regioselective synthesis of 1,2‐difunctionalized arenes with the formation of C(sp 3 )− and C(sp 2 )−C(arene) bonds. 2‐Iodobenzoic acid derivatives behave as masked bifunctional reagent (BFR) and react with 2‐pyridyl‐methyl sulfoximine (MPyS) protected aliphatic acids bearing α,α‐disubstituted groups, and alkenes to produce β‐aryl‐δ‐alkenyl amide derivatives in a single operation. The transformation involves Pd(II)/Pd(IV) and Pd(II)/Pd(0) catalytic systems. Detailed mechanistic studies, including density functional theory (DFT) calculations, reveal the formation of large T‐shaped palladacycles and the onset of a 1,2‐palladium migration via decarboxylation.

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hal-04587172 , version 1 (24-05-2024)

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Arghadip Ghosh, Koneti Kondalarao, Arijit Saha, Vincent Gandon, Akhila Sahoo. A Three‐Component Arene Difunctionalization: Merger of C(sp 3 )/(sp 2 )−H Bond Addition. Angewandte Chemie International Edition, 2023, 62 (51), ⟨10.1002/anie.202314395⟩. ⟨hal-04587172⟩
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