Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels–Alder Reactions

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Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E1/2(C*/C•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (Ep/2 = 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.