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Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [Cu II (dmp) 2 Cl]Cl
Author(s) -
Engl Sebastian,
Reiser Oliver
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900839
Subject(s) - chemistry , photocatalysis , photoredox catalysis , copper , catalysis , photochemistry , visible spectrum , reaction mechanism , combinatorial chemistry , styrene , radical , organic chemistry , copolymer , physics , polymer , optoelectronics
The Cu II complex [Cu II (dmp) 2 Cl]Cl (dmp = 2,9‐dimethyl‐1,10‐phenanthroline) is evaluated as an oxidation stable precursor for visible‐light‐mediated Cu I ‐photoredox catalysis, being efficient and considerable more cost‐effective compared to previously established copper(I) photocatalysts. Its performance and efficiency are demonstrated within a broad scope of atom transfer radical addition (ATRA) reactions, allowing the 1,2‐difunctionalization of alkenes, as well as for decarboxylative coupling and an Appel reaction. Moreover, the utility of the complex is shown by various gram‐scale functionalizations of styrene, thus suggesting [Cu II (dmp) 2 Cl]Cl to be a low‐priced alternative precatalyst for processes run on scale. Furthermore, this study provides UV/Vis evidence on the mechanism for the visible light activation of Cu II complexes.