e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Trifluoromethylation of various aromatic compounds by CF 3 I in the presence of Fe (II) compound, H 2 O 2 and dimethylsulfoxide

T Kino, Y Nagase, Y Ohtsuka, K Yamamoto…

Index: Kino, Tatsuhito; Nagase, Yu; Ohtsuka, Yuhki; Yamamoto, Kyoko; Uraguchi, Daisuke; Tokuhisa, Kenji; Yamakawa, Tetsu Journal of Fluorine Chemistry, 2010 , vol. 131, # 1 p. 98 - 105

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Citation Number: 116

Abstract

Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe (II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five- membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as ...

2-Aminopyrimidine Structure

2-Aminopyrimidine

Iodotrifluoromethane Structure

Iodotrifluoromethane

~21%

5-(Trifluoromethyl)-2-pyrimidinamine Structure

5-(Trifluoromet...

2-Amino-1,3,4-thiadiazole Structure

2-Amino-1,3,4-t...

Iodotrifluoromethane Structure

Iodotrifluoromethane

~32%

2-Amino-5-Trifluoromethyl-1,3,4-Thiadiazole Structure

2-Amino-5-Trifl...

Aminopyrazine Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~58%

3-(Trifluoromethyl)-2-pyrazinamine Structure

3-(Trifluoromet...

Coumarone Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~29%

2-(trifluoromethyl)-1-benzofuran Structure

2-(trifluoromet...

Iodotrifluoromethane Structure

Iodotrifluoromethane

2-Chloroaniline Structure

2-Chloroaniline

~39%

2-Chloro-6-(trifluoromethyl)aniline Structure

2-Chloro-6-(tri...

2-Chloro-4-(trifluoromethyl)aniline Structure

2-Chloro-4-(tri...

Iodotrifluoromethane Structure

Iodotrifluoromethane

Thianaphthene Structure

~16%

2-(trifluoromethyl)-1-benzothiophene Structure

2-(trifluoromet...

Pyrazole Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~25%

3-(Trifluoromethyl)pyrazole Structure

3-(Trifluoromet...

Iodotrifluoromethane Structure

Iodotrifluoromethane

2,6-Dichloroaniline Structure

2,6-Dichloroaniline

~38%

2,6-Dichloro-4-(trifluoromethyl)aniline Structure

2,6-Dichloro-4-...

Indole Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~%

2-Trifluoromethyl-1H-indole Structure

2-Trifluorometh...

3-Trifluoromethyl-1H-indole Structure

3-Trifluorometh...

Furan Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~16%

2-(trifluoromethyl)furan Structure

2-(trifluoromet...

Iodotrifluoromethane Structure

Iodotrifluoromethane

4-Chlorophenol Structure

~37%

4-Chloro-2-(trifluoromethyl)phenol Structure

4-Chloro-2-(tri...

Bromothiophene Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~46%

2-Bromo-5-(trifluoromethyl)thiophene Structure

2-Bromo-5-(trif...

leucoline Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~9%

5-(Trifluoromethyl)quinoline Structure

5-(Trifluoromet...

8-Aminoquinoline Structure

8-Aminoquinoline

Iodotrifluoromethane Structure

Iodotrifluoromethane

~18%

8-amino-7-(trifluoromethyl)quinoline Structure

8-amino-7-(trif...

5-trifluoromethyl-8-quinolinamine Structure

5-trifluorometh...

Detail

Iodotrifluoromethane Structure

Iodotrifluoromethane

2-Chloroaniline Structure

2-Chloroaniline

~27%

2-Chloro-6-(trifluoromethyl)aniline Structure

2-Chloro-6-(tri...

2-Chloro-4-(trifluoromethyl)aniline Structure

2-Chloro-4-(tri...

Iodotrifluoromethane Structure

Iodotrifluoromethane

Structure

~7%

4-Aminobenzotrifluoride Structure

4-Aminobenzotri...

2-Aminobenzotrifluoride Structure

2-Aminobenzotri...

Pyrrole Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~74%

2-(trifluoromethyl)-1H-pyrrole Structure

2-(trifluoromet...

Pyridin-3-ol Structure

Iodotrifluoromethane Structure

Iodotrifluoromethane

~43%

2-(Trifluoromethyl)-3-pyridinol Structure

2-(Trifluoromet...