Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer-Type Transformation

被引：13

作者：

Wang, Xi ^{[1
]}

Xu, Yan ^{[1
]}

Zhou, Yujing ^{[1
]}

Zhang, Yan ^{[1
]}

Wang, Jianbo ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci BNLMS,Minist Educ, Beijing 100871, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 16期

关键词：

trifluoromethylation; aromatic amines; diazonium salts; silver; Sandmeyer reaction; PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; SILVER-MEDIATED TRIFLUOROMETHYLATION; BORONIC ACIDS; ARYLBORONIC ACIDS; SYNTHETIC METHODS; DIAZONIUM SALTS; ALKYL NITRITES; ARYL STANNANES; ARENES; PERFLUOROALKYLATION;

D O I：

10.1055/s-0033-1338659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions.

引用

收藏

页码：2143 / 2148

页数：6

相关论文

共 59 条

[1] On aromatic fluoric compounds, I A new method for its representation [J].

Balz, G ;

Schiemann, G .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190

[2] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[3] The Trifluoromethylating Sandmeyer Reaction: A Method for Transforming C-N into C-CF3 [J].

Browne, Duncan L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1482-1484

[4] METHYL-3-OXO-OMEGA-FLUOROSULFONYLPERFLUOROPENTANOATE - A VERSATILE TRIFLUOROMETHYLATING AGENT FOR ORGANIC HALIDES [J].

CHEN, QY ;

DUAN, JX .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1389-1391

[5] METHYL FLUOROSULFONYLDIFLUOROACETATE - A NEW TRIFLUOROMETHYLATING AGENT [J].

CHEN, QY ;

WU, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :705-706

[6] 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

[7] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[8] Pd-Catalyzed Oxidative ortho-C-H Borylation of Arenes [J].

Dai, Hui-Xiong ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :134-137

[9] Copper-Promoted Sandmeyer Trifluoromethylation Reaction [J].

Dai, Jian-Jun ;

Fang, Chi ;

Xiao, Bin ;

Yi, Jun ;

Xu, Jun ;

Liu, Zhao-Jing ;

Lu, Xi ;

Liu, Lei ;

Fu, Yao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) :8436-8439

[10] Sandmeyer Trifluoromethylation of Arenediazonium Tetrafluoroborates [J].

Danoun, Gregory ;

Bayarmagnai, Bilguun ;

Gruenberg, Matthias F. ;

Goossen, Lukas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :7972-7975

← 1 2 3 4 5 6 →