Redox-Neutral Rh(III)-Catalyzed Olefination of Carboxamides with Trifluoromethyl Allylic Carbonate

被引：15
|
作者：
Park, Jihye [1 ]
Han, Sangil [1 ]
Jeon, Mijin [1 ]
Mishra, Neeraj Kumar [1 ]
Lee, Seok-Yong [1 ]
Lee, Jong Suk [3 ]
Kwak, Jong Hwan [1 ]
Um, Sung Hee [2 ]
Kim, In Su [1 ]
机构：
[1] Sungkyunkwan Univ, Sch Med, Samsung Biomed Res Inst, Sch Pharm, Suwon 16419, South Korea
[2] Sungkyunkwan Univ, Sch Med, Samsung Biomed Res Inst, Dept Mol Cell Biol, Suwon 16419, South Korea
[3] Bioctr, Gyeonggi Inst Sci & Technol Promot, Suwon 443270, South Korea
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期
基金：
新加坡国家研究基金会;
关键词：
COPPER-CATALYZED TRIFLUOROMETHYLATION; C-H ALLYLATION; LIGHT PHOTOREDOX CATALYSIS; BOND FORMATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; OLEFINIC TRIFLUOROMETHYLATION; TERMINAL ALKENES; ROOM-TEMPERATURE; ORGANIC HALIDES;
D O I：
10.1021/acs.joc.6b02485
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rhodium(III)-catalyzed olefination of various carboxamides with alpha-CF3-substituted allylic carbonate is described. This reaction provides direct access to linear CF3-allyl frameworks with complete trans-selectivity. In particular, a rhodium catalyst provided Heck-type gamma-CF3-allylation products via the beta-O-elimination of rhodacycle intermediate and subsequent olefin migration process.
引用
收藏
页码：11353 / 11359
页数：7
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