3 years ago

Regiodivergent Visible Light-Induced C–H Functionalization of Quinolines at C-5 and C-8 under Metal-, Photosensitizer- and Oxidant-Free Conditions

Regiodivergent Visible Light-Induced C–H Functionalization of Quinolines at C-5 and C-8 under Metal-, Photosensitizer- and Oxidant-Free Conditions
Percia Beatrice Arockiam, Lucas Guillemard, Joanna Wencel-Delord
A general strategy towards the selective perfluoroalkylation of quinoline derivatives at C-5 and C-8 is described. This exceptionally mild radical transformation, compatible with a large panel of substrates, does not require any transition metal catalysts or oxidants. Outstandingly, visible light photoinduction using simple household bulbs, in the absence of a photosensitizer, is the unique activation mode. Further importance of this reaction relies on its capacity to functionalize selectively both C-5 and C-8 positions of quinolines. This transformation, perfectly fulfilling green chemistry requirements, allows a truly practical and straightforward access to a variety of unprecedented functionalized amino- and amidoquinoline skeletons, presenting attractive features for medicinal and agrochemical industry.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700471

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