Vicinal bromostannanes as novel building blocks for the preparation of di- and trisubstituted imidazoles

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…130 Revesz et al have synthesised the 4,5-disubstituted imidazole 65, a potent anti-inflammatory drug, using the SM cross-coupling reaction as a key step. 131 Aryl-substituted pyridines are an important class of compounds in medicinal chemistry and materials science. In this regard, Finney and co-workers prepared the 2,4,6-trisubstituted pyridines 66 by using a stepwise SM crosscoupling reaction of the corresponding trihalopyridine and the arylboronic acids.…”

Polyarylated Thiazoles via a Combined Halogen Dance – Cross‐Coupling Strategy

“…These lower yields with vicinal bromostannanes of azoles were not surprising. Revesz and co-workers [26] reported imidazole examples which gave similar low yields (24-55 %). Only in one case the desired product was obtained in 74 % yield.…”

Five‐Membered Heterocycles: 1,3‐Azoles

“…Other examples of Stille couplings using 2-substituted 5-stannylimidazoles [290] are applicable to the synthesis of cytotoxic agents [291] and an imidazolyl isomer of the alkaloid didemnimide C [292]. 5-Stannylimidazoles have also been prepared by a 2,5-dilithiation, followed by a double stannylation and a 2-hydrodestannylation sequence [291].…”