4.7 Article

Dehydrogenative Transformations of Imines Using a Heterogeneous Photocatalyst

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 11, Pages 5959-5965

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00617

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Funding

  1. ACS Petroleum Research Fund
  2. Purdue University
  3. Davidson School of Chemical Engineering

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Heterogeneous semiconductors are underexploited as photoredox catalysts, in organic synthesis relative to their homogeneous, molecular-counterparts. Here, we report the use of metal/TiO2 particles as catalysts for light-induced dehydrogenative imine transformations. The highly oxophilic nature of the TiO2 surface promotes the selective binding and dehydrogenation of alcohols in the presence of other oxidizable and Lewis basic functional groups. This feature enables the clean photogeneration of aldehyde equivalents that can be utilized in multicomponent couplings.

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