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 photoreductions. Its successful applications in the aerobic oxidative hydroxylation of arylboronic acids and in the oxidation of benzylic C(sp³)–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⁺][BF₄ ^–]

5 Applications of [ ⁿ Pr-DMQA⁺][BF₄ ^–] in Red-Light-Induced Photocatalysis

6 Conclusion

Key words

photocatalysis - helical carbenium ions - organic photoredox catalyst - red-light-induced reactions - photooxidation - photoreduction

Publication History

Received: 10 September 2020

Accepted after revision: 20 September 2020

Article published online:
12 October 2020

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