Palladium-catalyzed through-space C(sp(3))-H and C(sp(2))-H bond activation by 1,4-palladium migration: efficient synthesis of [3,4]-fused oxindoles.

Tiffany Piou (1) , Ala Bunescu , Qian Wang , Luc Neuville (1) , Jieping Zhu

1 ICSN - Institut de Chimie des Substances Naturelles

Palladium two step: Linear anilides were converted into the title compounds in good to excellent yields through a palladium-catalyzed domino carbopalladation/1,4-palladium shift sequence. The C(sp(3) )-H activation involves a seven-membered palladacycle, and is chemoselective in the presence of competitive C(sp(2) )H bonds. DMA=N,N-dimethylacetamide, OPiv=pivalate.

Domaines: Chimie organique

Tiffany Piou, Ala Bunescu, Qian Wang, Luc Neuville, Jieping Zhu. Palladium-catalyzed through-space C(sp(3))-H and C(sp(2))-H bond activation by 1,4-palladium migration: efficient synthesis of [3,4]-fused oxindoles.. Angewandte Chemie International Edition, 2013, 52 (47), pp.12385-12389. ⟨10.1002/anie.201306532⟩. ⟨hal-00933392⟩