Commonly used SO2 replacement reagents include Na2SO3, Na2S2O5 (or K2S2O5), HOCH2SO2Na·2H2O and DABSO, etc. Among them, Na2SO3 needs to be used in combination with concentrated sulfuric acid, and the process of releasing SO2 will generate severe heat; inorganic sulfate salts often require high temperature and phase transfer catalysts; HOCH2SO2Na·2H2O is highly hygroscopic and can easily form sodium sulfite, sodium thiosulfate, sodium sulfide, etc. Decomposition products; DABCO, an organic base produced after DABSO releases SO2, may affect the main reaction system.
Professor Lian Zhong of Sichuan University has developed a new type of exogenous SO2 replacement reagent - SOgen, which has the advantages of being cheap, stable, controllable and easy to store. When used in combination with the "two-chamber" system developed by Skrydstrup, it can be basically used within 5 minutes. Completely releases SO2 and prevents the generated organic matter from affecting the main reaction system. This reagent has been successfully used in many reactions such as olefin sulfonyl functionalization, aryl chloride sulfonation, electrophilic cross-coupling, asymmetric sulfonylation, etc., and has achieved good results [1-12].

How to use

Figure 1 How to use SOgen reagent

Place the SOgen reagent in the reactor, add an equivalent of p-toluene, use tetradecane as the solvent (1.0 mL/0.2 mmol SOgen), seal and react at 100°C for 10 minutes. The reaction ends when the reaction solution becomes clear.

Application examples

Figure 2 SOgen reagent is used in the palladium-catalyzed direct sulfamate reaction of aryl iodides and amines [1]

Figure 3 SOgen reagent applied in copper-catalyzed enantioselective arylsulfonyl cyanation reaction of vinylarenes[8]

Professor Lian Zhong, professor and doctoral supervisor at the National Key Laboratory of Biotherapy/Dermatology, West China Hospital of Sichuan University, was selected into the National Overseas High-level Young Talent Project (Youth Thousand Talents). Currently, he is mainly engaged in research on the resource utilization of sulfur dioxide, mechanochemistry, and the design and synthesis of small molecule targeted drugs. In recent years, he has presided over the National Natural Science Foundation of China projects, the National Youth Thousand Talents Program, Sichuan Provincial Science and Technology Projects, etc. He has published many papers as the corresponding/first author in famous international journals such as Science, Nat. Commun., Angew. Chem. Int. Ed., ACS Catal., etc., and currently serves as an international editorial board member of the European Journal of Organic Chemistry.

Bailingwei exclusively supplies the new exogenous SO2 replacement reagent developed by Professor Lian Zhong of Sichuan University. The product advantages are as follows: It can avoid the generated organic matter from affecting the main reaction system; SO2 releases quickly, is cheap and controllable, and has a wide range of applications; Stable in nature and easy to store;

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References

1. Angew. Chem. Int. Ed. 2021, 60, 7353-7359.
2. Org. Lett. 2021, 23, 4991-4996.
3. Org. Chem. Front. 2021,8, 5310-5315.
4. Org. Lett. 2021, 23, 5880-5884.
5. Org. Lett. 2022, 24, 1207-1212.
6. RSC Adv. 2022, 12, 16745-16750.
7. Adv. Synth. Catal. 2022, 364, 2729-2734.
8. ACS Catal. 2022, 12, 10764-10770.
9. Org. Lett. 2022, 24, 7560-7565.
10. Org. Chem. Front. 2023, 10, 3239-3244.
11. Org. Chem. Front. 2023, 10, 3567-3576.
12. Org. Lett. 2023, 25, 5916-5921.