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 Ala Bunescu Qian Wang Luc Neuville Jieping Zhu

Angew Chem Int Ed Engl

Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch.

Published: November 2013

Linear anilides were transformed into specific compounds using a palladium-catalyzed reaction with high efficiency.
The process involves a unique sequence of carbopalladation and a 1,4-palladium shift, which is crucial for the reaction's success.
Notably, the reaction selectively activates C(sp(3))-H bonds even when C(sp(2))-H bonds are present, utilizing a seven-membered palladacycle in the process.

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.

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http://dx.doi.org/10.1002/anie.201306532	DOI Listing

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