Regioselective hydroboration-oxidation and -amination of fluoro-substituted styrenes

Hydroboration of fluorinated styrenes with common hydroborating agents results in polymerization. However, regioselective hydroboration has been achieved by utilizing iodoborane-dimethyl sulfide. A series of fluorinated β-phenethyl alcohols and amines were synthesized via this methodology.

A simple and highly regioselective preparation of β-fluoroaryl organoboranes and their conversion to the corresponding fluorinated alcohols and amines in very high yields has been described. Figure optionsDownload as PowerPoint slide