Iron- or Copper-Catalyzed Trifluoromethylation of Acrylamide-Tethered Alkylidenecyclopropanes: Facile Synthesis of CF3-Containing Polycyclic Benzazepine Derivatives

被引：99

作者：

Yu, Liu-Zhu ^{[1
,2
]}

Xu, Qin ^{[1
,2
]}

Tang, Xiang-Yiang ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ACS CATALYSIS | 2016年 / 6卷 / 02期

基金：

中国国家自然科学基金;

关键词：

iron or copper catalysis; alkylidenecyclopropanes; tetracyclic benzazepine derivatives; radical addition; activated alkenes; ring opening; BOND FORMATION; INTRAMOLECULAR CYCLIZATION; DEAROMATIZATION ACCESS; CONVENIENT ACCESS; ACTIVATED ALKENES; EFFICIENT; AMINOTRIFLUOROMETHYLATION; METHYLENECYCLOPROPANES; CONSTRUCTION; FLUORINE;

D O I：

10.1021/acscatal.5b02400

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A novel iron- or copper-catalyzed trifluoromethylation of acrylamide-tethered alkylidenecyclopropanes with Togni reagent II to construct CF3-containing tetracyclic benzazepine derivatives under mild and convenient conditions has been disclosed. The chemoselective addition of in situ generated trifluoromethyl radical onto the activated alkenes triggers the reaction followed by a ring-opening process of alkylidenecyclopropanes, leading to the formation of two types of CF3-containing tetracyclic benzazepine derivatives in moderate to good yields, respectively, with excellent functional group tolerance.

引用

页码：526 / 531

页数：6

共 89 条

[51] Good Partnership between Sulfur and Fluorine: Sulfur-Based Fluorination and Fluoroalkylation Reagents for Organic Synthesis [J].