Radical C-H 18F-difluoromethylation of heteroarenes with [18F]difluoromethyl heteroaryl-sulfones by visible light photoredox catalysis was written by Lemos, Agostinho Luis Pereira;Trump, Laura;Lallemand, Benedicte;Pasau, Patrick;Mercier, Joel;Lemaire, Christian;Monbaliu, Jean-Christophe;Genicot, Christophe;Luxen, Andre. And the article was included in Catalysts in 2020.Electric Literature of C7H4N2O2S2 This article mentions the following:
Six new [18F]difluoromethyl heteroaryl-sulfones ArSO2CF[18F] [Ar = 5-methoxybenzothiazol-2-yl, N-methylbenzimidazol-2-yl, 1-phenyltetrazol-5-yl, etc.] were prepared and, based on overall radiochem. yields (RCYs), three of these reagents ArSO2CF[18F] [6-methoxy-1,3-benzothiazol-2-yl, 6-nitro-1,3-benzothiazol-2-yl, 1-phenyltetrazol-5-yl] were selected for fully automated radiosynthesis on a FASTlab synthesizer (GE Healthcare) at high level of starting radioactivity. Subsequently, their efficiency as 18F-difluoromethylating reagents was evaluated using antiherpetic drug acyclovir as a model substrate. The results showed that introduction of mol. modifications in structure of previously reported ArSO2CF[18F] [Ar = benzothiazol-2-yl] influenced amount of fac-IrIII(ppy)3 and residence time needed to ensure a complete C-H 18F-difluoromethylation process. The photocatalytic C-H 18F-difluoromethylation reaction with selected reagents was extended to other heteroarenes. Radical-trapping experiments demonstrated likely involvement of radical species in C-H 18F-difluoromethylation process. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Electric Literature of C7H4N2O2S2).
5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C7H4N2O2S2
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica