Scientists of the ZIOC have proposed a new photochemical method for the synthesis of thiols

Thiols and disulfides are important intermediates for the synthesis of various pharmaceutically important sulfur compounds. In the last decade, approaches to the formation of carbon-sulfur bonds, which proceed through the formation of various S-centered radicals, have been actively developed. These methods often require fewer synthetic steps and make it possible to obtain structures that are otherwise difficult to obtain.

For several years, scientists from the Laboratory of Functional Organic Compounds of the ZIOC have been conducting research on the use of the perfluorinated pyridinylthio group (PyfS) as a convenient photoredox-active moiety for a wide variety of photochemical transformations. In one of their recent works, the researchers succeeded in photoredox-catalyzed cleavage of the C-S bond between the sulfur atom and the perfluoropyridinium fragment in the presence of the N-heterocyclic carbene-borane complex (NHC-BH3). The reaction proceeds through the formation of thiyl radicals, which are transformed to free thiols. The developed approach makes it possible to convert alkanes, alkenes, and carboxylic acids into thiols in two synthetic photochemical steps. The resulting thiols can be transformed without isolation into the corresponding disulfides or sulfur alkylation products.

Source:

Liubov I. Panferova, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N‑Heterocyclic Carbene−Borane // Org. Lett. 2022, 24, 46, 8559–8563. DOI: 10.1021/acs.orglett.2c03585.