4.8 Article

LiBr-promoted photoredox neutral Minisci hydroxyalkylations of quinolines with aldehydes

Journal

GREEN CHEMISTRY
Volume 22, Issue 23, Pages 8233-8237

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0gc01872d

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Funding

  1. Hunan Provincial Science and Technology Department [2019RS2039]
  2. National Natural Science Foundation of China [21502161, 21602187]
  3. Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization

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Photoredox-neutral hydroxyalkylations of quinolines with aldehydes, induced by sustainable visible light under mild conditions, are described. Non-toxic and inexpensive LiBr is found to be the key for the success of the atom-economical Minisci method. Combined with a highly oxidative photocatalyst and visible light irradiation, the bromide additive mediates the H abstraction/acyl radical formation directly from aldehydes. The present mild photoredox neutral protocol provides an important alternative, especially for the challenging Minisci hydroalkylations, as well as a promising approach for atom-economical Minisci reactions with broader N-heterocycle spectra.

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