Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C-H and C-C Bond Cleavage

被引：9
|
作者：
Ano, Yusuke [2 ,3 ]
Takahashi, Daichi [1 ]
Yamada, Yuki [1 ]
Chatani, Naoto [1 ]
机构：
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Fac Engn, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[3] Osaka Univ, Ctr Atom & Mol Technol, Grad Sch Engn, Suita, Osaka 5650871, Japan
来源：
ACS CATALYSIS | 2023年 / 13卷 / 04期
关键词：
palladium; N-heterocyclic carbenes; cyclobutanones; skeletal rearrangement; C-C activation; C-H activation; CARBON-CARBON; ACTIVATION; MIGRATION; COMPLEXES; HYDROGEN; ARYL; HECK;
D O I：
10.1021/acscatal.2c06389
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The palladium-catalyzed skeletal rearrangement of 3-arylcyclobutanones into 1-indanones is reported. A Pd(0)/IMes catalyst allows for the cleavage of C(carbonyl)-C(sp3) and C(sp2)-H bonds to result in the skeletal rearrangement, and neither an extra reactive functional group nor a directing group is required to promote the reaction. Deuterium-labeling experiments indicate that the C-C bond is initially activated and that the subsequent C-H activation is involved in the rate-determining step.
引用
收藏
页码：2234 / 2239
页数：6
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