Complex-induced proximity effect in the regioselective lithiation of pyridine derivatives

Article abstract of DOI:10.1002/ejoc.201101592

The regioselective ring lithiation of BF₃-complexed 3-picoline (1a), 3,4-lutidine (1b), and 3,5-lutidine (1c) was studied. The dilithiation of 1a, 1b, and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex-induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.