Beilstein J. Org. Chem.2025,21, 253–261, doi:10.3762/bjoc.21.17
-derived Functional Oligosaccharides Engineering Technology Research Center of Anhui Province, Fuyang Normal University, Fuyang, Anhui, 236037, P. R. China 10.3762/bjoc.21.17 Abstract A new synthetic method for disulfides and 3-sulfenylchromones is reported. This innovative approach is based on the
tetrabutylammonium iodide (TBAI)/H2SO4 reduction system using sodium sulfinate as key component, thus eliminating the need for thiols and redox reagents commonly used in traditional methods. Various disulfides and 3-sulfenylchromones were obtained in moderate to excellent yields through this methodology. Mechanistic
studies indicate that thiosulfonates play an important role in the reaction process.
Keywords: disulfides; sodium sulfinates; 3-sulfenylchromones; TBAI; thiosulfonates; Introduction
Organosulfur compounds containing S–S bonds, often referred to as disulfides, are among the most valuable functional
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Graphical Abstract
Scheme 1:
Different strategies for the synthesis of disulfides and 3-sulfenylchromones.
Beilstein J. Org. Chem.2017,13, 2017–2022, doi:10.3762/bjoc.13.199
, free of any strong oxidants and neutral reaction conditions.
Methods on the synthesis of 3-sulfenylchromones.
Scope of the 3-sulfenylated chromone synthesis. General conditions: 1 (0.3 mmol), 2 (0.36 mmol), KIO3 (0.15 mmol) in 2 mL DMF, stirred at 130 °C for 24 h; yield of isolated product based on 1
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Graphical Abstract
Scheme 1:
Methods on the synthesis of 3-sulfenylchromones.