Synthesis of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process

被引:184
作者
Pinto, Artur [1 ]
Neuville, Luc [1 ]
Retailleau, Pascal [1 ]
Zhu, Jieping [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1021/ol062022h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4927 / 4930
页数:4
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