AI Article Synopsis
- A new light-driven catalytic process is introduced for creating 3-pyrrolines using a combination of disulfide assistance and selenium catalysts, achieving yields up to 95%.
- The method effectively converts a variety of sulfonamides with diverse olefinic structures while maintaining good tolerance for functional groups.
- Mechanistic studies reveal that the disulfide co-catalyst plays a dual role: it acts as an electron shuttle and enhances the final product release step, leading to better yields.
Article Abstract
A light-driven dual and ternary catalytic aza-Wacker protocol for the construction of 3-pyrrolines by partially disulfide-assisted selenium-π-acid multicatalysis is reported. A structurally diverse array of sulfonamides possessing homopolar mono-, di- and trisubstituted olefinic double bonds is selectively converted to the corresponding 3-pyrrolines in up to 95 % isolated yield and with good functional group tolerance. Advanced electrochemical mechanistic investigations of the protocol suggest a dual role of the disulfide co-catalyst. On the one hand, the disulfide serves as an electron hole shuttle between the excited photoredox catalyst and the selenium co-catalyst. On the other hand, the sulfur species engages in the final, product releasing step of the catalytic cycle by accelerating the β-elimination of the selenium moiety, which was found in many cases to lead to considerably improved product yields.
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| http://dx.doi.org/10.1002/cssc.202301518 | DOI Listing |
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Article Synopsis
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- The method effectively converts a variety of sulfonamides with diverse olefinic structures while maintaining good tolerance for functional groups.
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