Reactions of CF3-substituted boranes with α-diazocarbonyl compounds

Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)2 and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with α-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction.

Trifluoromethylation of methyl boronic esters followed by reaction with α-diazocarbonyl compounds is described.Figure optionsDownload as PowerPoint slide