Graf, Sebastian and Pesch, Henner and Appleson, Theresa and Lei, Tao and Breder, Alexander and Siewert, Inke (2024) Mechanistic Analysis Reveals Key Role of Interchalcogen Multicatalysis in Photo-Aerobic 3-Pyrroline Syntheses by Aza-Wacker Cyclizations. CHEMSUSCHEM, 17 (9). e202301518. ISSN 1864-5631, 1864-564X
Full text not available from this repository. (Request a copy)Abstract
A light-driven dual and ternary catalytic aza-Wacker protocol for the construction of 3-pyrrolines by partially disulfide-assisted selenium-pi-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 beta-elimination of the selenium moiety, which was found in many cases to lead to considerably improved product yields. A light-driven multicatalytic aza-Wacker protocol for the construction of 3-pyrrolines is reported. A structurally diverse array of sulfonamides possessing homopolar mono-, di- and trisubstituted CC 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 suggest a dual role of the disulfide co-catalyst.+ image
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | EXPEDIENT SYNTHESIS; HECK-CYCLIZATIONS; ALKENES; DERIVATIVES; AMINATION; ROUTE; FUNCTIONALIZATION; AMINOPALLADATION; CYCLOADDITION; PYRROLIDINES; Photocatalysis; Molecular electrochemistry; Synthetic methods; Selenium; Organocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Alexander Breder |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 13 Jan 2026 10:49 |
| Last Modified: | 13 Jan 2026 10:49 |
| URI: | https://pred.uni-regensburg.de/id/eprint/64210 |
Actions (login required)
 |
View Item |
