Long-Range Halogen Dance Reaction in 4,5-Dihalogeno-2-(Sulfur-Containing Heterocyclyl)thiazole
Year: 2024
Type: article
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 P4-t-Bu to induce the halogen dance reaction.
Authors: Yoshimi Hirokawa, Kenji Arimitsu, Yuriko Ikegawa, Taiga Kashihara, Mizuki Kosuda, Airi Miura, Naoyoshi Maezaki
Institution: Osaka Ohtani University
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4405301471