Access to indolines from primary phenylethylamines by an unexpected palladium-catalyzed C-H functionalization process.

A new method for the preparation of 2,2-disubstituted indolines from 2-phenylethylamines was developed under Pd catalysis and PhI(OAc) 2 as oxidant. Imines derived from 2-pyridinecarboxaldehyde were formed in situ to direct a C-H activation process. The resulting imines were also oxidized to the corresponding amides in the same Pd-catalyzed process to obtain the final indoline as a picolinamide.