Ru-catalyzed activation of sp3 C–O bonds: O- to N-alkyl migratory rearrangement in pyridines and related heterocycles

Abstract

We report a novel strategy for the formal activation of sp³ C–O bonds under Ru catalysis. In this reaction, an O-alkylpyridine undergoes migratory rearrangement to its corresponding N-alkylpyridone via coordination of the Lewis basic N atom. This transformation represents the first generalcatalytic approach to O- to N-alkyl migration in N-containing heterocycles. Extension of this methodology to other heterocycles, including O-alkylpyridazines and O-alkylazoles, was achieved.