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

被引：67

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

页码：2859 / 2866

页数：8

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