Palladium‐Catalyzed Through‐Space C(sp3)H and C(sp2)H Bond Activation by 1,4‐Palladium Migration: Efficient Synthesis of [3,4]‐Fused Oxindoles

2013/09/17 by Tiffany Piou, Ala Bunescu, Qian Wang +2 · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Catalytic Cross-Coupling Reactions #Synthesis and Catalytic Reactions

paper · doi:10.1002/anie.201306532

openalex publication_date 2013/09/17 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/29

Abstract

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.

Citations

• High-Yielding Palladium-Catalyzed Intramolecular Alkane Arylation: Reaction Development and Mechanistic Studies
• Pd-Catalyzed Alkyl to Aryl Migration and Cyclization: An Efficient Synthesis of Fused Polycycles via Multiple C−H Activation
• C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions

Cited by

• Zhu Jieping [wikipedia]