Pd-catalyzed bicyclization of 2-alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans: a DFT study

被引：3

作者：

Yang, Liu ^{[1
]}

Ren, Gerui ^{[1
]}

Ye, Xinchen ^{[1
]}

Que, Xianyong ^{[1
]}

Lei, Qunfang ^{[2
]}

Fang, Wenjun ^{[2
]}

Xie, Hujun ^{[1
]}

机构：

[1] Zhejiang Gongshang Univ, Dept Appl Chem, Hangzhou 310035, Zhejiang, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2014年 / 27卷 / 03期

基金：

中国博士后科学基金; 美国国家科学基金会;

关键词：

DFT; palladium catalysis; propargylic alcohol; reaction mechanism; reductive elimination; FORMING REDUCTIVE ELIMINATION; CROSS-COUPLING REACTIONS; BIARYL SYNTHESIS; HECK REACTION; PALLADIUM; MECHANISM; POLARIZATION; FLUORINATION; MIGRATION; ENERGIES;

D O I：

10.1002/poc.3271

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of palladium-catalyzed bicyclization of 2-alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans has been studied computationally with the aid of density functional theory (DFT). Full free energy profiles are computed for different reaction equations between different reaction substrates. The calculation results showed that the catalytic cycle is found to contain six steps, oxidative addition, ligand substitution, first CC triple bond insertion, rearrangement, second CC triple bond insertion and reductive elimination, with the reductive elimination being the rate-determining step for the different reaction equations (1), (2) and (3). Our calculations are consistent with experimental observations. Copyright (c) 2014 John Wiley & Sons, Ltd.

引用

页码：237 / 244

页数：8

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