The C–H coupling of aromatic heterocycles with bis (pinacolato) diboron was carried out in octane at 80–100° C in the presence of a 1/2 [IrCl (COD)] 2-(4, 4′-di-tert-butyl-2, 2′- bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively ...
[Paul, Sulagna; Chotana, Ghayoor A.; Holmes, Daniel; Reichle, Rebecca C.; Maleczka Jr., Robert E.; Smith III, Milton R. Journal of the American Chemical Society, 2006 , vol. 128, # 49 p. 15552 - 15553]