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
收藏
页码：2859 / 2866
页数：8
相关论文
共 150 条
[1]  
A. K. P. Corporation, 2009, U. S. Patent, Patent No. [2009/48223A1, 200948223, 200,948,223 A1]
[2]   PHOTOCHEMICAL TRIFLUOROMETHYLATION OF SOME AROMATIC AND HETEROAROMATIC-COMPOUNDS WITH TRIFLUOROMETHYL BROMIDE [J].
AKIYAMA, T ;
KATO, K ;
KAJITANI, M ;
SAKAGUCHI, Y ;
NAKAMURA, J ;
HAYASHI, H ;
SUGIMORI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) :3531-3537
[3]  
Andrei P., 2013, U. S. Patent, Patent No. [2013/96083A1, 201396083]
[4]  
[Anonymous], 2005, ANGEW CHEM, V117, P196
[5]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201107414
[6]  
Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/nchem.1727, 10.1038/NCHEM.1727]
[7]   On the synthesis of vinyl isonitriles [J].
Baldwin, JE ;
Chen, DQ ;
Russell, AT .
CHEMICAL COMMUNICATIONS, 1997, (24) :2389-2390
[8]   Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].
Ball, Nicholas D. ;
Kampf, Jeff W. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+
[9]  
Besset T., 2012, ANGEW CHEM, V124, P5134
[10]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
12345678910