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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
