Unsymmetrical azines are useful functional materials. The synthesis of unsymmetrical azines via iminyl radical N-N bond cross-coupling is dramatically challenging compared with the N-N homocoupling. The balance of two different iminyl radical intermediates is crucial. The control of the selectivity of N-N coupling over the N-abstraction of a hydrogen atom is also vital. A dual functional photocatalyst is the key to access the synergistic energy transfer (EnT)-single-electron transfer (SET) relay (EnT triggered SET) which can work both as an EnT PC and as a SET PC. In this work, by the strategy of synergistic EnT-SET relay catalyzed by the single dual functional organophotocatalyst , the cross coupling of two different amyl iminyl radicals for the synthesis of unsymmetrical azines has been achieved. A twisted carbazole-cored highly electron-rich heterocycle plays dual roles as an EnT and SET organophotocatalyst.
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Photocatalytic One-Step Synthesis of Unsymmetrical Azines.
Org Lett
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Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
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Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8530, Japan.
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