Regiospecific Synthesis of 1-Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion

被引：65
|
作者：
Cheng, Yuanzheng [1 ]
Yuan, Xiangai [2 ]
Jiang, Heng [1 ]
Wang, Ruzhi [1 ]
Ma, Jing [2 ]
Zhang, Yan [1 ]
Yu, Shouyun [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
[2] Nanjing Univ, Inst Theoret & Computat Chem, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 13期
关键词：
iridium; isocyanides; isoquinolines; photochemistry; trifluoromethylation; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; C-H TRIFLUOROMETHYLATION; DE-NOVO SYNTHESIS; CATALYZED TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; EFFICIENT SYNTHESIS; BOND FORMATION; METAL-FREE; OXIDATIVE TRIFLUOROMETHYLATION; RADICAL TRIFLUOROMETHYLATION;
D O I：
10.1002/adsc.201400504
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A strategy has been developed for the regiospecific synthesis of 1-trifluoromethylisoquinoline derivatives. This strategy is enabled by a photoredox vinyl isocyanide insertion with the help of Umemoto's reagent. The methodology presented here provides an access to highly fuctionalized 1-trifluoromethylisoquinolines regiospecifically under mild conditions in good-to-excellent chemical yields. A detailed mechanism is proposed, which is supported by experiments and theoretical calculations.
引用
收藏
页码：2859 / 2866
页数：8
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