化学
区域选择性
钯
双功能
芳基
试剂
酰胺
药物化学
脱羧
催化作用
串联
组合化学
立体化学
有机化学
烷基
材料科学
复合材料
作者
Arghadip Ghosh,Koneti Kondalarao,Arijit Saha,Vincent Gandon,Akhila K. Sahoo
标识
DOI:10.1002/anie.202314395
摘要
A tandem three-component C-H bond addition involving the activation of an inert C(sp3)-H bond is reported. The process enables the direct regioselective synthesis of 1,2-difunctionalized arenes with the formation of C(sp3)- and C(sp2)-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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