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Metal-free formal carbon–halogen bond insertion: facile syntheses of 3-halo 3,3′-disubstituted oxindoles and spirooxindole-γ-butyrolactones

2017; Royal Society of Chemistry; Volume: 53; Issue: 51 Linguagem: Inglês

10.1039/c7cc03765a

1364-548X

Rong Zhou, Rongfang Liu, Kai Zhang, Ling Han, Honghui Zhang, Wen‐Chao Gao, Ruifeng Li,

Cyclopropane Reaction Mechanisms

A novel P(NMe2)3-mediated formal carbon-halogen bond insertion of isatins into allylic and benzylic bromides/chlorides has been realized, leading to a facile synthesis of 3-halo 3,3'-disubstituted oxindoles. This reaction relies on the unique dual nucleophilic-electrophilic reactivity pattern of the Kukhtin-Ramirez adduct via a cascade SN2-SN2 process. It also represents a rare metal-free approach for carbon-halogen bond insertion. Upon treatment with trifluoroacetic acid, spirooxindole-γ-butyrolactones have been efficiently prepared from the corresponding insertion products.