5 years ago

Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals
Niels H. Damrauer, Haishen Yang, Matthew D. Ryan, Chern-Hooi Lim, Steven M. Sartor, Ryan M. Pearson, Garret M. Miyake, Ya Du
Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible-light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible-light PCs for trifluoromethylation reactions and dual photoredox/nickel-catalyzed C−N and C−S cross-coupling reactions, both of which have been historically exclusive to precious metal PCs. The new iridium! The photophysical and electrochemical properties of a strongly reducing dihydrophenazine and phenoxazine enable their application as visible light photoredox catalysts to catalyze reactions that were previously restricted to precious metals. These organic visible light photoredox catalysts not only present sustainable alternatives to precious metals, but can possess enhanced properties to their metal counterparts for catalysis (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702926

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