Sulfur-containing compounds occupy a very important position in the fields of food science, life science, pharmaceutical science, and materials science. However, the synthesis of sulfur-containing compounds presents many challenges [1]:

Traditional methods of preparing sulfur-containing compounds use mercaptans and thiophenols, which not only have an unpleasant odor, but also often deactivate the catalyst due to their coordination with metal catalysts;
In the synthesis of asymmetric disulfides, symmetric disulfide by-products are easily generated;
The dissulfide bond has a low dissociation energy and is easily broken during the conversion process.

Figure 1: General structural formula of Bunte salt
Bunte salt has stable properties, no unpleasant odor, and is almost non-toxic. It can be used as an important sulfur source. In addition to generating thiols under acidic conditions or disulfide under oxidation, in recent years, Jiang Xuefeng’s research group at East China Normal University has A series of new Bunte salts have also been researched and developed, and their application scope has been greatly expanded.

Figure 1: General structural formula of Bunte salt

Example 1 Simultaneous sulfonation and oxidation through mild photocatalysis to generate the corresponding thioethers and sulfoxides respectively

Figure 2: Bunte salt reacts to form thioether and sulfoxide [2]

Selective vulcanization/sulfonation • Late stage sulfoxides • Cascade electron and energy transfer • Mild diaryl sulfoxide synthesis

Example 2 Add potassium sulfide and chloroform as raw materials to synthesize thiocarbonyl substitutes in one pot

Figure 3: One-pot synthesis of dithiocarbamates from Bunte salt [3]

Can generate multiple bonds such as C=S, C-S, S-S at one time • Replaces volatile and flammable CS2, environmentally friendly • Can produce gram-level products

Example 3 Through different cross-coupling reactions, thioethers and thioesters are generated respectively.

Figure 4 Using Bunte salt to generate thioethers and thioesters[4]

Avoid the use of mercaptans, odorless • Green, efficient • Mild reaction conditions

Example 4 Diastereoselective synthesis of α-thioglycosides by metal palladium-catalyzed allylic rearrangement

Figure 5 Diastereoselective synthesis of thioglycosides using Bunte salt and metal palladium [5]

Avoids the deactivation of metal palladium •Breaks through the selectivity problem of glycosidic bond construction •Can derive a variety of functional groups

1. Wang M , X J iang. Prospects and Challenges in Organosulfur Chemistry. 2022.
2. Yiming Li, Ming Wang, Xuefeng Jiang. ACS Catal.2017, 7, 11, 7587-7592.
3. Wei Tan, Niklas Jänsch, Tina Öhlmann, Franz-Josef Meyer-Almes, Xuefeng Jiang. Org. Lett. 2019, 21, 18, 7484-7488.
4. Zongjun Qiao, Xuefeng Jiang. Org. Lett. 2016, 18, 7, 1550-1553
5. Li J , Wang M , Jiang X . Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement. 2021.