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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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AMER CHEMICAL SOC
DOI: 10.1021/jacs.3c08883
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Chemodivergent synthesis is achieved in asymmetric photocatalysis using a dual catalyst system consisting of a chiral phosphoric acid and DPZ as a photosensitizer. Different inorganic bases enable the formation of valuable products from the three-component radical tandem transformations. The distinct pKa environment plays a key role in the success of this process.
Chemodivergent synthesis has been achieved in asymmetric photocatalysis. Under a dual catalyst system consisting of a chiral phosphoric acid and DPZ as a photosensitizer, different inorganic bases enabled the formation of two sets of valuable products from the three-component radical tandem transformations of 2-bromo-1-arylenthan-1-ones, styrenes, and quinoxalin-2(1H)-ones. The key to success was the distinct pK a environment, in which the radicals that formed on the quinoxalin-2(1H)-one rings after two radical addition processes underwent either single-electron oxidation or single-electron reduction. In addition, this work represents the first use of quinoxalin-2(1H)-ones in asymmetric photoredox catalysis.
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