Catalyst-free direct C-H trifluoromethylation of arenes in water-acetonitrile

被引：40

作者：

Wang, Dangui ^{[1
]}

Deng, Guo-Jun ^{[1
]}

Chen, Shiya ^{[1
]}

Gong, Hang ^{[1
]}

机构：

[1] Xiangtan Univ, Coll Chem, Minist Educ, Key Lab Environm Friendly Chem & Applicat, Xiangtan 411105, Peoples R China

来源：

GREEN CHEMISTRY | 2016年 / 18卷 / 22期

基金：

中国国家自然科学基金;

关键词：

PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; HETEROAROMATIC-COMPOUNDS; ROOM-TEMPERATURE; SANDMEYER TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; AROMATIC-COMPOUNDS; HETEROARENES; FLUORINE; TRIFLUOROMETHANESULFINATE;

D O I：

10.1039/c6gc02000c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a mild and practical strategy for the catalyst-free trifluoromethylation of arenes using the inexpensive solid sodium triflinate (Langlois' reagent, NaSO2CF3) as a trifluoromethyl (CF3) source and solid sodium persulfate as an initiator. The reaction is environmentally friendly and proceeds at 30 degrees C in a water-acetonitrile mixture. This transformation can be easily scaled up to the gram level with excellent yield.

引用

页码：5967 / 5970

页数：4

共 50 条

[1] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].

Alonso, Concepcion ;

Martinez de Marigorta, Eduardo ;

Rubiales, Gloria ;

Palacios, Francisco .

CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935

[2]

[Anonymous], ADV FLUORINE CHEM

[3] Clinical pharmacology of artemisinin-based combination therapies [J].

Aweeka, Francesca T. ;

German, Polina L. .

CLINICAL PHARMACOKINETICS, 2008, 47 (02) :91-102

[4] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].

Ball, Nicholas D. ;

Gary, J. Brannon ;

Ye, Yingda ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584

[5] 2'-SUBSTITUTED CHALCONE DERIVATIVES AS INHIBITORS OF INTERLEUKIN-1 BIOSYNTHESIS [J].

BATT, DG ;

GOODMAN, R ;

JONES, DG ;

KERR, JS ;

MANTEGNA, LR ;

MCALLISTER, C ;

NEWTON, RC ;

NURNBERG, S ;

WELCH, PK ;

COVINGTON, MB .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) :1434-1442

[6] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].

Charpentier, Julie ;

Frueh, Natalja ;

Togni, Antonio .

CHEMICAL REVIEWS, 2015, 115 (02) :650-682

[7] Rapid and Efficient Trifluoromethylation of Aromatic and Heteroaromatic Compounds Using Potassium Trifluoroacetate Enabled by a Flow System [J].

Chen, Mao ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11628-11631

[8]

Chen P., 2013, SYNTHESIS-STUTTGART, P2919

[9] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

[10] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304

← 1 2 3 4 5 →