Long-Range Halogen Dance Reaction in 4,5-Dihalogeno-2-(Sulfur-Containing Heterocyclyl)thiazole

Abstract

We have investigated the base-induced long-range halogen dance reactions of 4,5-dibromo- or 4-bromo-5-iodothiazoles bearing sulfur-containing aromatic heterocycles at the C2-position. We have found that the reaction occurs in bithiazole regioisomers or (thiophenyl)thiazole derivatives, in which the C-5 halo group on the thiazole halogen donor regioselectively migrates to a halogen acceptor ring after treatment with lithium bis(trimethylsilyl)amide. The substrate with a thiophen-2-yl substituent required highly basic P<inf>4</inf>-t-Bu to induce the halogen dance reaction.

Keywords: biheterocyclic compound; halogen acceptor; halogen donor; long-range halogen dance reaction.