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CC BY 4.0 · SynOpen 2023; 07(01): 76-87
DOI: 10.1055/s-0040-1720060
graphical review

Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review

Logan R. Beck 
a   Department of Chemistry, Columbia University, New York, New York, 10027, USA
,
Katherine A. Xie
a   Department of Chemistry, Columbia University, New York, New York, 10027, USA
,
Samantha L. Goldschmid
a   Department of Chemistry, Columbia University, New York, New York, 10027, USA
,
Stavros K. Kariofillis 
a   Department of Chemistry, Columbia University, New York, New York, 10027, USA
,
Candice L. Joe 
b   Chemical Process Development, Bristol Myers Squibb, New Brunswick, New Jersey, 08903, USA
,
Trevor C. Sherwood 
c   Small Molecule Drug Discovery, Bristol Myers Squibb, Princeton, New Jersey, 08543, USA
,
Melda Sezen-Edmonds 
b   Chemical Process Development, Bristol Myers Squibb, New Brunswick, New Jersey, 08903, USA
,
Tomislav Rovis  ∗
a   Department of Chemistry, Columbia University, New York, New York, 10027, USA
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Abstract

Photoredox catalysis has revolutionized synthetic chemistry in recent decades. However, the field has traditionally used high-energy blue/ultraviolet light to activate chromophores. High-energy irradiation is associated with several drawbacks (e.g., activation of sensitive functional groups, undesired metal-ligand homolysis, background activation of molecules, and poor penetration), which has led researchers to develop alternative systems with lower energy deep red (DR) or near-infrared (NIR) light. This graphical review provides a concise overview of photophysical principles relevant to photoredox catalysis. Several applications that benefit from low-energy irradiation, such as large-scale batch reactions, photodynamic therapy, biological labeling, and multi-photon excitation are reviewed.

Key words

photoredox catalysis - deep red and near-infrared light - cross-coupling - reaction engineering - photodynamic therapy - photoaffinity labeling - proximity labeling - multiphoton excitation


Publication History

Received: 11 January 2023

Accepted: 24 January 2023

Article published online:
28 February 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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