Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives

被引：15
|
作者：
Chen, Cuili [1 ]
Chen, Xianxiao [1 ]
Zhang, Xiaoxiang [1 ]
Wang, Shifa [1 ]
Rao, Weidong [1 ]
Chan, Philip Wai Hong [2 ,3 ]
机构：
[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China
[2] Monash Univ, Sch Chem, Clayton, Vic, Australia
[3] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 24期
基金：
澳大利亚研究理事会; 中国国家自然科学基金;
关键词：
dehydrogenative cycloisomerization; 3,5-disubstituted phenols; 1,4-enyne esters; gold; homogeneous catalysis; C-H BONDS; CLOSING OLEFIN METATHESIS; META-SUBSTITUTED PHENOLS; AEROBIC DEHYDROGENATION; OXIDATIVE TRANSFORMATION; HYDROAROMATIC SYSTEMS; EFFICIENT SYNTHESIS; PROPARGYLIC ESTERS; COUPLING CDC; ACID;
D O I：
10.1002/adsc.201701068
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771.
引用
收藏
页码：4359 / 4368
页数：10
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