Synthesis of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process.
[reaction: see text] A highly efficient palladium-catalyzed synthesis of unsymmetrically substituted 3-(diarylmethylenyl)indolinones from readily accessible starting materials is developed. The domino reaction involves a sequence of intermolecular carbopalladation, C-H activation, and C-C bond formation. A plausible mechanistic pathway for the reaction is discussed on the basis of the kinetic isotope effect [K(H)/K(D) (intermolecular) = 1, K(H)/K(D) (intramolecular) = 2.7] as well as the electronic effect.
Pinto
Artur
A
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Neuville
Luc
L
Retailleau
Pascal
P
Zhu
Jieping
J