Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis

被引：170

作者：

Yasu, Yusuke ^{[1
]}

Koike, Takashi ^{[1
]}

Akita, Munetaka ^{[1
]}

机构：

[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 20期

关键词：

ELECTROPHILIC TRIFLUOROMETHYLATION; ASYMMETRIC FLUORINATION; HIGHLY EFFICIENT; PHOTOCATALYSIS; EMISSION; ACIDS;

D O I：

10.1039/c3cc39235j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile synthesis of trifluoromethylated alkenes by the radical-mediated trifluoromethylation of vinyltrifluoroborates has been developed. Togni's reagent serves as a CF3 radical precursor in the presence of the photoredox catalyst [Ru(bpy)(3)](PF6)(2) under visible light irradiation. This new photocatalytic protocol can be applicable to a wide variety of vinylborates containing electronically diverse substituents and hetero-aromatics.

引用

页码：2037 / 2039

页数：3

共 52 条

[31] On the remarkable antitumor properties of fludelone: How we got there [J].

Rivkin, A ;

Chou, TC ;

Danishefsky, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (19) :2838-2850

[32]

Selby T. P., 1995, PCT International Patent Application, Patent No. [5389600 A, 5389600]

[33] Aggregation induced emission (AIE) of trifluoromethyl substituted distyrylbenzenes [J].

Shi, Zhengwei ;

Davies, Joshua ;

Jang, Sei-Hum ;

Kaminsky, Werner ;

Jen, Alex K. -Y. .

CHEMICAL COMMUNICATIONS, 2012, 48 (63) :7880-7882

[34] Recent advances in enantioselective trifluoromethylation reactions [J].

Shibata, Norio ;

Mizuta, Satoshi ;

Torn, Takeshi .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (03) :215-228

[35] Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective [J].

Shibata, Norio ;

Matsnev, Andrej ;

Cahard, Dominique .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6

[36] Modern synthetic methods for fluorine-substituted target molecules [J].

Shimizu, M ;

Hiyama, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :214-231

[37] Synthesis and Photophysical Properties of Dimethoxybis(3,3,3-trifluoropropen-1-yl)benzenes: Compact Chromophores Exhibiting Violet Fluorescence in the Solid State [J].

Shimizu, Masaki ;

Takeda, Youhei ;

Higashi, Masahiro ;

Hiyama, Tamejiro .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (09) :2536-2544

[38] 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: Minimal Fluorophores Exhibiting Highly Efficient Emission in the Solid State [J].

Shimizu, Masaki ;

Takeda, Youhei ;

Higashi, Masahiro ;

Hiyama, Tamejiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3653-3656

[39] A "Renaissance" in Radical Trifluoromethylation [J].

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :8950-8958

[40] PHOTOREDOX CATALYSIS BY [Ru(bpy)3]2+ TO TRIGGER TRANSFORMATIONS OF ORGANIC MOLECULES. ORGANIC SYNTHESIS USING VISIBLE-LIGHT PHOTOCATALYSIS AND ITS 20th CENTURY ROOTS [J].

Teply, Filip .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (07) :859-917

← 1 2 3 4 5 6 →