jo061324u_si_001.pdf (2.69 MB)
Linchpin Synthons: Metalation of Aryl Bromides Bearing a Potassium Trifluoroborate Moiety
journal contribution
posted on 2006-09-15, 00:00 authored by Gary A. Molander, Noel M. EllisAryl bromides bearing a potassium trifluoroborate moiety
were subjected to lithium−halogen exchange at low temperature using a variety of alkyllithium reagents. A number
of different electrophiles were evaluated in their reactions
with the aryllithiums produced therein. Under carefully
optimized conditions, potassium bromophenyl trifluoroborates afforded good to excellent yields of the corresponding
alcohols (64−94% isolated yield) when aldehydes or ketones
were used as the electophilic partner. Esters were unfortunately found to be unreactive.