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

页码：11353 / 11359

页数：7

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