Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis

The emergence of visible light photoredox catalysis has enabled the productive use of lower energy radiation, leading to highly selective reaction platforms. Polypyridyl complexes of iridium and ruthenium have served as popular photocatalysts in recent years due to their long excited state lifetimes...

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Published inJournal of organic chemistry Vol. 81; no. 16; pp. 7244 - 7249
Main Authors Joshi-Pangu, Amruta, Lévesque, François, Roth, Hudson G, Oliver, Steven F, Campeau, Louis-Charles, Nicewicz, David, DiRocco, Daniel A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.08.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
ORGANIC-SYNTHESIS
ALKENES
COMPLEX
LIGHT
FLOW PHOTOCHEMISTRY
ANTI-MARKOVNIKOV HYDROAMINATION
CARBOXYLIC-ACIDS
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Summary:The emergence of visible light photoredox catalysis has enabled the productive use of lower energy radiation, leading to highly selective reaction platforms. Polypyridyl complexes of iridium and ruthenium have served as popular photocatalysts in recent years due to their long excited state lifetimes and useful redox windows, leading to the development of diverse photoredox-catalyzed transformations. The low abundances of Ir and Ru in the earth’s crust and, hence, cost make these catalysts nonsustainable and have limited their application in industrial-scale manufacturing. Herein, we report a series of novel acridinium salts as alternatives to iridium photoredox catalysts and show their comparability to the ubiquitous [Ir­(dF-CF3-ppy)2(dtbpy)]­(PF6).
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01240