Photo-oxidative Cross-Dehydrogenative Coupling-Type Reaction of Thiophenes with α-Position of Carbonyls Using a Catalytic Amount of Molecular Iodine was written by Sudo, Yusuke;Yamaguchi, Eiji;Itoh, Akichika. And the article was included in Organic Letters in 2017.Application In Synthesis of 5-Phenylthiazole This article mentions the following:
Substituted thiophenes and thiazoles such as I (R = Me, Ph, 4-MeC6H4, 4-MeOC6H4, 4-O2NC6H4, 4-OHCC6H4, 4-MeO2CC6H4, PhCOOCH2) underwent regioselective and chemoselective photochem. aerobic dehydrogenative coupling with 1,1,1-tricarbonyl compounds such as (EtO2C)2CHR1 (R1 = EtO2C, Me2NCO, PhSO2) in the presence of I2 and K3PO4 in MeCN/H2O (and in the absence of added metals) under irradiation by compact fluorescent lamps to give substituted thienyl and thiazolyl tricarbonyl compounds such as II (R = Me, Ph, 4-MeC6H4, 4-MeOC6H4, 4-O2NC6H4, 4-OHCC6H4, 4-MeO2CC6H4, PhCOOCH2; R1 = EtO2C, Me2NCO, PhSO2). The coupling reaction did not occur in the absence of light or in the presence of radical inhibitors, and II (R = Me; R1 = EtO2C) was formed from coupling of 2-methylthiophene and IC(CO2Et)3 in the absence of iodine; a mechanism for the coupling reaction is proposed. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).
5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Application In Synthesis of 5-Phenylthiazole
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica