The deprotonation of 2-methoxypyridine was attempted using putative (TMP) 3FeLi prepared from different iron sources. Using iodine to intercept the metalated 2- methoxypyridine, the best result was obtained from FeBr2 (1equiv) using THF at room temperature; nevertheless, in addition to the expected iodide, the corresponding 2, 2′- dimer was obtained (86% total yield). The origin of the competitive formation of the 2, 2′- ...
[Diaz-Valenzuela, M. Belen; Phillips, Scott D.; France, Marcia B.; Gunn, Mary E.; Clarke, Matthew L. Chemistry - A European Journal, 2009 , vol. 15, # 5 p. 1227 - 1232]