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Mechanistic Analysis Reveals Key Role of Interchalcogen Multicatalysis in Photo-Aerobic 3-Pyrroline Syntheses by Aza-Wacker Cyclizations.

Authors :
Graf S
Pesch H
Appleson T
Lei T
Breder A
Siewert I
Source :
ChemSusChem [ChemSusChem] 2024 May 08; Vol. 17 (9), pp. e202301518. Date of Electronic Publication: 2024 Jan 31.
Publication Year :
2024

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.<br /> (© 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1864-564X
Volume :
17
Issue :
9
Database :
MEDLINE
Journal :
ChemSusChem
Publication Type :
Academic Journal
Accession number :
38214219
Full Text :
https://doi.org/10.1002/cssc.202301518