Categories: S-S Bond Formation >
Synthesis of Thiosulfonates
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.