期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 -, 期 -, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202314395
关键词
1,2-Difunctionalization; Bifunctional Reagent; DFT Studies; Multicomponent Reaction; Pd(II) Catalyst
A tandem three-component C-H bond addition involving the activation of an inert C(sp(3))-H bond is reported. The reaction enables the direct regioselective synthesis of 1,2-difunctionalized arenes. Mechanistic studies reveal the reaction pathway.
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 alpha,alpha-disubstituted groups, and alkenes to produce beta-aryl-delta-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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