Helical Carbenium Ion-Based Organic Photoredox Catalyst: A Versatile and Sustainable Option in Red-Light-Induced Reactions

Abstract The development of a sustainable catalytic system for red-light-induced photocatalysis is presented. The catalytic system consists of a helical carbenium ion-based organic photoredox catalyst (PC) that is capable of using low-energy red light (λ max = 640 nm) for both photooxidations and ph...

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Bibliographic Details
Published in:Synlett 2021-03, Vol.32 (4), p.337-334
Main Authors: Mei, Liangyong, Gianetti, Thomas
Format: Article
Language:English
Subjects:
synpacts
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Summary:Abstract The development of a sustainable catalytic system for red-light-induced photocatalysis is presented. The catalytic system consists of a helical carbenium ion-based organic photoredox catalyst (PC) that is capable of using low-energy red light (λ max = 640 nm) for both photooxidations and photoreductions. Its successful applications in the aerobic oxidative hydroxylation of arylboronic acids and in the oxidation of benzylic C(sp 3 )–H bonds (reductive quenching), as well as in dual transition-metal/organocatalyzed C–H arylations and intermolecular atom-transfer radical additions (oxidative quenching) provide further support for its role as a versatile and efficient organic PC. 1 Introduction 2 Red-Light-Induced Photocatalysis 3 Properties of N , N ′-Dipropyl-1,13-dimethoxyquinacridinium Tetrafluoroborate 4 Two Proposed Representative Catalytic Cycles of [ n Pr-DMQA + ][BF 4 – ] 5 Applications of [ n Pr-DMQA + ][BF 4 – ] in Red-Light-Induced Photocatalysis 6 Conclusion
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1705942