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A New Approach to Nitrones through Cascade Reaction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis

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posted on 15.05.2015, 00:00 by Cheng-Wei Lin, Bor-Cherng Hong, Wan-Chen Chang, Gene-Hsiang Lee
A series of nitroalkanes were efficiently transformed to alkylnitrones using a visible light irradiation photocatalytic process. The mild, efficient, and environmentally benign reaction method, involving dynamic reciprocations of cascade pathways, comprises a mixture of a Ru­(bpy)3Cl2 photoredox catalyst and DIPIBA or Hünig’s base in CH3CN. Notably, DIPIBA was found to be the best additive for the cross condensation reaction of nitroalkanes with aldehydes. The structures of appropriate products were confirmed by X-ray analysis.