Mechanism of the Palladium-Catalyzed Addition of Arylboronic Acids to Enones: A Computational Study

被引：42
|
作者：
Lan, Yu [1 ]
Houk, K. N. [1 ]
机构：
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 12期
基金：
美国国家科学基金会;
关键词：
ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CONJUGATE ADDITION; ASYMMETRIC 1,4-ADDITION; HECK REACTION; ARYL; BOND; DFT; KETONES; ENERGY;
D O I：
10.1021/jo2002903
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium(II)-catalyzed addition of arylboronic acids to beta,beta-disubstituted enones has been investigated with the BP86 density functional. The results show that the mechanism requires three steps: transmetalation, alkene insertion, and protonation. The alkene insertion is the rate-determining step. For unactivated alkenes, the Heck-type beta-hydride elimination is more favored than protonation.
引用
收藏
页码：4905 / 4909
页数：5
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