Synthesis of α-Quaternary Bicyclopentanes through Synergistic Organophotoredox and Hydrogen Atom Transfer Catalysis. Journal of the American Chemical Society 2021, 143

Metal-Free Hydrosilylation Polymerization by Merging Photoredox and Hydrogen Atom Transfer Catalysis.

Zhujun Huang, Zhe Chen, Yuan Jiang, Ning Li, Shicheng Yang, Guowei Wang, Xiangcheng Pan.

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis. Shin, Brian Koronkiewicz, Guanqi Qiu, Robert R. Photoinduced Phosphorylation/Cyclization of Cyanoaromatics for Divergent Access to Mono- and Diphosphorylated Polyheterocycles.

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Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α-(Trifluoromethyl)styrenes. Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation.

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Based on their preeminent electrochemical and photophysical characteristics, all novel, purely organic photoredox catalysts were evaluated in three challenging, mechanistically distinct classes of benchmark reactions (either requiring balanced, highly oxidizing or strongly reducing properties) to demonstrate their enormous potential as customizable photocatalysts, that outperform and complement prevailing typical best photocatalysts. Especially halogen arene core substitutions are instrumental for our targeted alterations of the catalysts’ redox properties. Systematic modifications of both the donor substituents as well as the acceptors’ molecular core allowed us to identify strongly oxidizing as well as strongly reducing catalysts (e.g., for an unprecedented detriflation of unactivated naphthol triflate), which additionally offer remarkably balanced redox potentials with predictable trends. Herein, we demonstrate the successful implementation of a rational design strategy for a series of deliberate structural manipulations of cyanoarene-based, purely organic donor–acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene ( 4CzIPN) as a starting point. The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations.

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