Organolithium chemistry: Transmetallation, electrophilic substitution, and cross-coupling reactions of organolithium with boron trifluoride

by Trana, Carol J.; Gawley, Robert E.

Research has demonstrated that potassium organotrifluoroborates can be formed via electrophilic substitution reactions and that they make stable intermediates in cross-coupling reactions. However, α-lithiated piperidines have been shown to be excellent nucleophiles for transmetallation and electrophilic substitution reactions. Our efforts to synthesize a lithium organotrifluoroborate using an α-lithiated piperidine, as well as subsequent cross-coupling reactions utilizing this compd. are presented.