Categories: C-S Bond Formation >
Synthesis of thioesters
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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.
Direct
photocatalyzed hydrogen atom transfer enables a three-component coupling of aldehydes, alkenes, or alkynes and elemental sulfur. This carbonyl thiyl
radical-based thioester synthesis represents an orthogonal
strategy to the conventional thiol-based nucleophilic substitution and exhibits
a remarkably broad substrate scope.
H. Tang, M. Zhang, Y. Zhang, P. Luo, D. Ravelli, J. Wu, J. Am. Chem. Soc.,
2023, 145, 5846-5854.
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.
An ambient-light-promoted stereospecific olefinic C(sp2)-S bond
construction of thioacids with 1,1-diarylethenes provides various (Z)-vinyl
thioesters in good yields under solvent- and catalyst-free conditions.
Mechanistic studies indicated that the formation of thioacid-olefin complexes is
responsible for generating carbonyl thiyl radicals and O2
participates as a traceless reagent.
R. Wang, J.-L. Yuan, J.-L. Liang, J.-Y. Hu, Q. Fu, F.-S. Liang, J. Org. Chem., 2024, 89,
9597-9608.