Categories: S-S Bond Formation >
Synthesis of Thiosulfonates
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Recent Literature
A convenient and efficient synthesis of thiosulfonates in very good yields from
thiols and sodium sulfinates involves iron(III)-catalyzed formation of sulfenyl
and sulfonyl radicals in situ under aerobic conditions and their subsequent
cross-coupling. The utilization of readily available, nontoxic, and inexpensive
iron(III) as a catalyst and atmospheric oxygen as an oxidant makes this process
green and sustainable.
T. Keshari, R. Kapoorr, L. D. S. Yadav,
Synlett, 2016, 27, 1878-1882.
A copper-catalyzed sulfonylation of disulfides using sodium sulfinates in air
formed various sulfur-sulfone bonds efficiently and afforded thiosulfonates in
good yields. Selenosulfonates could also be prepared.
N. Taniguchi, J. Org. Chem.,
2015,
80, 1764-1765.
Tert-butyl hydroperoxide (TBHP) mediates a coupling of
sulfonylhydrazides with thiols in the presence of CuBr2 as catalyst
to afford thiosulfonates via a radical process.
G.-Y. Zhang, S.-S. Lv, A. Shoberu, J.-P. Zou, J. Org. Chem.,
2017, 82, 9801-9807.
Selectfluor mediates practical and efficient oxidations of sulfides and
thiols to provide sulfoxides, sulfones, and thiosulfonates, respectively, at
ambient temperature. All these organosulfur compounds can be prepared with
nearly quantitative yields by applying eco-friendly H2O as O-source.
The formation of sulfoxides and thiosulfonates takes only a few minutes.
X. Guo, X. Sun, M. Jiang, Y. Zhao, Synthesis, 2022, 54,
1996-2004.
o-Iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP) mediate
the conversion of thiols to thiosulfonates at rt. DMP is better than IBX in
terms of reaction rate, conversion, and required equivalents. IBX-mediated
oxidation of benzyl thiols produced thiosulfonates, whereas DMP afforded O-benzyl
esters.
A. Chandra, N. Yadav, S. Payra, K. N. Parida, Org. Lett., 2023, 25,
6256-6261.