Direct, Regiospecific 2-Lithiation of Pyridines and Pyridine 1-Oxides with in Situ Electrophilic Trapping

Article abstract of DOI:10.1021/jo00170a071

Efficient synthetic routes to 2-substituted pyridines and 2,6-disubstituted pyridine 1-oxides involving direct lithiation with the sterically hindered base lithium 2,2,6,6-tetramethylpiperidide (LiTMP) in the presence of electrophiles that are compatible with the base, e.g., trimethylsilyl chloride (Me3SiCl) and hexafluoroacetone (HFA), are described.