Photoredox catalysis harvesting multiple photon or electrochemical energies

Beilstein J Org Chem. 2023 Jul 28:19:1055-1145. doi: 10.3762/bjoc.19.81. eCollection 2023.

Abstract

Photoredox catalysis (PRC) is a cutting-edge frontier for single electron-transfer (SET) reactions, enabling the generation of reactive intermediates for both oxidative and reductive processes via photon activation of a catalyst. Although this represents a significant step towards chemoselective and, more generally, sustainable chemistry, its efficacy is limited by the energy of visible light photons. Nowadays, excellent alternative conditions are available to overcome these limitations, harvesting two different but correlated concepts: the use of multi-photon processes such as consecutive photoinduced electron transfer (conPET) and the combination of photo- and electrochemistry in synthetic photoelectrochemistry (PEC). Herein, we review the most recent contributions to these fields in both oxidative and reductive activations of organic functional groups. New opportunities for organic chemists are captured, such as selective reactions employing super-oxidants and super-reductants to engage unactivated chemical feedstocks, and scalability up to gram scales in continuous flow. This review provides comparisons between the two techniques (multi-photon photoredox catalysis and PEC) to help the reader to fully understand their similarities, differences and potential applications and to therefore choose which method is the most appropriate for a given reaction, scale and purpose of a project.

Keywords: consecutive photoinduced electron transfer; electro-activated photoredox catalysis; photoelectrochemistry; photoredox catalysis; radical ions.

Publication types

  • Review

Grants and funding

M. L. and J. P. B. are members of the Elite Network of Bavaria Doctoral College: “IDK Chemical Catalysis with Photonic or Electric Energy Input” and M. L. is grateful to the College for financial support. S. S. is grateful for funding provided by the University of Regensburg and the SynCat programme of the Elite Network of Bavaria. J. P. B. acknowledges funding provided by the Alexander von Humboldt Foundation within the framework of the Sofja Kovalevskaja Award endowed by the German Federal Ministry of Education and Research. J. P. B. is an associated member of DFG TRR 325 ‘Assembly Controlled Chemical Photocatalysis’ (444632635) and thanks other members of the TRR for insightful discussions.