Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ]
Johannes Morstein1, Haiyun Hou1, Chen Cheng1
1Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Abstract:
A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3 ] as the CF3 source under mild, oxidative conditions with high functional-group compatibility. This transformation complements prior trifluoromethylation of arenes in several ways. Most important, this method converts arylsilanes formed by the silylation of aryl C-H bonds to trifluoromethylarenes, thereby allowing the conversion of arenes to trifluoromethylarenes. The unique capabilities of the reported method are demonstrated by the conversion of a C-H bond into a C-CF3 bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.
Related Concept Videos
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition


