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Synthesis of Thiosulfonates


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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.