Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: scope, limitations, and mechanistic features

…, EC Escudero-Adán, P Novák, VV Grushin

Index: Lishchynskyi, Anton; Novikov, Maxim A.; Martin, Eddy; Escudero-Adan, Eduardo C.; Novak, Petr; Grushin, Vladimir V. Journal of Organic Chemistry, 2013 , vol. 78, # 22 p. 11126 - 11146

Full Text: HTML

Citation Number: 63

Abstract

Fluoroform-derived CuCF3 recently discovered in our group exhibits remarkably high reactivity toward aryl and heteroaryl halides, performing best in the absence of extra ligands. A broad variety of iodoarenes undergo smooth trifluoromethylation with the “ligandless” CuCF3 at 23–50° C to give the corresponding benzotrifluorides in nearly quantitative yield. A number of much less reactive aromatic bromides also have been trifluoromethylated, ...

 Related Synthetic Route

~99%

~94%

~56%

~74%

~33%

~77%

~88%

~91%

~%

~30%

~91%

~77%

~22%

~89%

~87%

~82%

~94%

~96%

~75%

~60%

~29%

~99%

~99%

~20%

~84%

~97%

~95%

~88%

~87%

~8%