The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines

The acid promoted addition of organotrifluoroborate salts to imine and enamine electrophiles is reported. Use of the pre-activated trifluoroboronate complex bypasses the need for alpha-hetero substitution on the electrophile component, greatly expanding the scope of the Petasis borono-Mannich reaction. A variety of vinyl, aromatic and heteroaromatic trifluoroborate salts undergo addition with good efficiency under mild reaction conditions. The reaction is amenable for use with a variety of carbamate protected imine and enamine electrophiles, achieving for the first time the effective coupling with aliphatic aldehydes.