Mechanism in palladium-catalyzed dearomative allylic reactions of benzyl phosphates with allyl borates: Insights from DFT calculations

被引：1
|
作者：
Ling, Menghang [1 ]
Yuan, Jingwang [1 ]
Song, Zhijun [1 ]
Gao, Jian [1 ]
Cao, Mengna [1 ]
Xie, Hujun [1 ]
机构：
[1] Zhejiang Gongshang Univ, Dept Appl Chem, Hangzhou 310018, Peoples R China
来源：
COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2020年 / 1191卷
基金：
中国国家自然科学基金;
关键词：
Palladium catalysis; Selectivity; Reaction mechanism; Dearomative reaction; Allylation; LIGAND; CHLOROMETHYLNAPHTHALENE; AROMATICITY; ALKYLATION; ENERGIES; INDOLES; DIMER;
D O I：
10.1016/j.comptc.2020.113030
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：
Dearomatic reactions are very important to build alicyclic moieties and expand the structural diversity. Muto and Yamaguchi recently investigated the Pd-catalyzed dearomative allylic reactions of allyl borates with benzyl phosphates to give final compounds. Herein, the calculations were conducted to explore the reaction mechanism and selectivity, and the results clarified that the dearomatic product through carbon-carbon bond formation between eta(3)-exo-(naphthyl)methyl para-carbon atom and allyl terminal carbon atom (TS3 = 7.3 kcal/mol) is energetically more favorable than the other carbon-carbon bond formation paths to afford aromatic and dearomatic compounds.
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页数：8
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