28519-34-8Relevant articles and documents
TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions
Huang, Cheng-Mi,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 1923 - 1926 (2020/01/13)
A TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols to construct thiosulfonates under transition-metal free conditions is reported. The thiosulfonates were isolated in good yields with broad tolerance of function
Metal-Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide
Li, Guoqing,Gan, Ziyu,Kong, Kexin,Dou, Xiaomeng,Yang, Daoshan
supporting information, p. 1808 - 1814 (2019/03/28)
A simple and catalyst-free strategy was developed for the synthesis of unsymmetrical thiosulfonates using readily available DABCO?(SO2)2 as a solid and bench-stable sulfur dioxide surrogate. The corresponding thiosulfonates were obtained through a radical pathway with good functional group tolerance. This strategy offers a promising synthesis method for the construction of diverse and useful thiosulfonates in the field of synthetic and pharmaceutical chemistry and extends the number of still limited sulfur dioxide fixation strategies. (Figure presented.).
Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate
Ali, Doaa,Hunter, Roger,De Doncker, Stephen,Rees-Jones, Sophie C. M.,Kaschula, Catherine H.
, p. 2862 - 2869 (2019/03/23)
New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 °C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.