Categories: C-S Bond Formation >
Synthesis of thioesters
A facile decarboxylative thioesterification of alkyl acid derived redox-active esters by merging photoredox catalysis and copper catalysis is applicable to a wide range of carboxylic acids. Moreover, product utilization is demonstrated with a direct transformation of thioesters to sulfonyl fluorides.
T. Xu, T. Cao, M. Yang, R. Xu, X. Nie, S. Liao, Org. Lett., 2020, 22, 3692-3696.
N-Thiohydroxy succinimide esters (NTSEs) are versatile reagents, serving as both acyl and acylthio surrogates for the diverse synthesis of ketones, thioesters, amides, and acyl disulfides by selective cleavage of similarly reactive C-S and N-S bonds.
Y.-F. Li, Y.-F. Wei, J. Tian, J. Zhang, H.-H. Chang, W.-C. Gao, Org. Lett., 2022, 24, 5736-5740.
The photocatalytic activation of elemental sulfur enables a mild, rapid, and chemoselective three-component thioesterification in the presence of olefins and α-ketoacids. This novel reaction is characterized by high yields and a broad substrate scope.
S. Murakami, T. Nanjo, Y. Takemoto, Org. Lett., 2021, 23, 7650-7655.
A visible-light-mediated deaminative thioesterification of amino acid derived Katritzky salts with thiobenzoic acid provides α-mercapto acid derivatives under mild conditions. This photoredox catalyst-free generation of alkyl radicals via C-N bond cleavage is enabled by the formation of an electron-donor-acceptor (EDA) complex between the Katritzky salt and thiobenzoic acid anion.
M. Yang, T. Cao, T. Xu, S. Liao, Org. Lett., 2019, 21, 8673-8678.