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Direct Transformation of Nitroalkanes to Nitriles Enabled by Visible-Light Photoredox Catalysis and a Domino Reaction Process.

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A mild and convenient process for direct transformation of nitroalkanes to the corresponding nitriles was developed using a visible-light photoredox catalysis strategy with household decorative blue LEDs and the additives… Click to show full abstract

A mild and convenient process for direct transformation of nitroalkanes to the corresponding nitriles was developed using a visible-light photoredox catalysis strategy with household decorative blue LEDs and the additives of Et3N and DIPIBA (or DIPEA). Application of the process in secondary nitroalkanes bearing a β-alcohol resulted in a domino process of the retro-Henry reaction and the subsequent acetalization, aldol, cyanohydrin, and ring-contraction reactions with stereoselectivities. The photocatalytic reaction was demonstrated by a continuous flow method.

Keywords: direct transformation; transformation nitroalkanes; light photoredox; visible light; process; reaction

Journal Title: Organic letters
Year Published: 2019

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