Silver-Mediated Trifluoromethylation of Aryldiazonium Salts: Conversion of Amino Group into Trifluoromethyl Group

A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is perfo...

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Published inJournal of the American Chemical Society Vol. 135; no. 28; pp. 10330 - 10333
Main Authors Wang, Xi, Xu, Yan, Mo, Fanyang, Ji, Guojing, Qiu, Di, Feng, Jiajie, Ye, Yuxuan, Zhang, Songnan, Zhang, Yan, Wang, Jianbo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.07.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Diazonium Compounds - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Methylation
Molecular Structure
Physical Sciences
Salts - chemistry
Science & Technology
Silver - chemistry
BORONIC ACIDS
ALKYL NITRITES
DIAZONIUM SALTS
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION
ARYL STANNANES
ARENES
CATALYZED TRIFLUOROMETHYLATION
SYNTHETIC METHODS
FLUORINATION
ARYLBORONIC ACIDS
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Summary:A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja4056239