Visible-light-mediated radical oxydifluoromethylation of olefinic amides for the synthesis of CF2H-containing heterocycles

被引：141

作者：

Fu, Weijun ^{[1
,2
]}

Han, Xin ^{[3
]}

Zhu, Mei ^{[1
,2
]}

Xu, Chen ^{[1
,2
]}

Wang, Zhiqiang ^{[1
,2
]}

Ji, Baoming ^{[1
,2
]}

Hao, Xin-Qi ^{[3
]}

Song, Mao-Ping ^{[3
]}

机构：

[1] Luoyang Normal Univ, Coll Chem & Chem Engn, Luoyang 471022, Henan, Peoples R China

[2] Luoyang Normal Univ, Henan Key Lab Funct Oriented Porous Mat, Luoyang 471022, Henan, Peoples R China

[3] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 91期

基金：

中国国家自然科学基金;

关键词：

DIRECT DIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; ARYL; ALKENES; INHIBITORS; FLUOROFORM; FLUORINE; ARYLDIFLUOROACETYLATION; FUNCTIONALIZATION;

D O I：

10.1039/c6cc07771d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The visible-light-mediated oxydifluoromethylation of olefinic amides with difluoromethyl sulfones has been explored. This method allows for an efficient and practical synthesis of a variety of CF2H-containing benzoxazines and oxazolines bearing various functional groups under mild conditions.

引用

页码：13413 / 13416

页数：4

共 75 条

[31]

Kirsch P., 2013, MODERN FLUOROORGANIC

[32] Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion [J].

Levin, Vitalij V. ;

Trifonov, Alexey L. ;

Zemtsov, Artem A. ;

Struchkova, Marina I. ;

Arkhipov, Dmitry E. ;

Dilman, Alexander D. .

ORGANIC LETTERS, 2014, 16 (23) :6256-6259

[33] Reactions of Difluorocarbene with Organozinc Reagents [J].

Levin, Vitalij V. ;

Zemtsov, Artem A. ;

Struchkova, Marina I. ;

Dilman, Alexander D. .

ORGANIC LETTERS, 2013, 15 (04) :917-919

[34] Synthesis of gem-Difluorocyclopropa(e)nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF2Br [J].

Li, Lingchun ;

Wang, Fei ;

Ni, Chuanfa ;

Hu, Jinbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (47) :12390-12394

[35] Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na and (CF2HSO2)2Zn via a Radical Process [J].

Li, Zejiang ;

Cui, Zili ;

Liu, Zhong-Quan .

ORGANIC LETTERS, 2013, 15 (02) :406-409

[36] Introduction of Fluorine and Fluorine-Containing Functional Groups [J].

Liang, Theresa ;

Neumann, Constanze N. ;

Ritter, Tobias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) :8214-8264

[37] Photoredox-Catalyzed Bromodifluoromethylation of Alkenes with (Difluoromethyl)triphenylphosphonium Bromide [J].

Lin, Qing-Yu ;

Ran, Yang ;

Xu, Xiu-Hua ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2016, 18 (10) :2419-2422

[38] Selective O-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents [J].

Liu, Guokai ;

Wang, Xin ;

Xu, Xiu-Hua ;

Lu, Xu ;

Tokunaga, Etsuko ;

Tsuzuki, Seiji ;

Shibata, Norio .

ORGANIC LETTERS, 2013, 15 (05) :1044-1047

[39] Synthesis of Oxindoles through Silver-Catalyzed Trifluoromethylation-, Difluoromethylation- and Arylsulfonylation-Cyclization Reaction of N-Arylacrylamides [J].

Liu, Jidan ;

Zhuang, Shaobo ;

Gui, Qingwen ;

Chen, Xiang ;

Yang, Zhiyong ;

Tan, Ze .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) :3196-3202

[40] Sandmeyer Difluoromethylation of (Hetero-)Arenediazonium Salts [J].

Matheis, Christian ;

Jouvin, Kevin ;

Goossen, Lukas J. .

ORGANIC LETTERS, 2014, 16 (22) :5984-5987

← 1 2 3 4 5 6 7 8 →