4 years ago

Oxyfunctionalization of the remote C-H bonds of aliphatic amines via decatungstate photocatalysis

Ian W. Davies, Huaming Sheng, Benjamin D. Sherry, Danielle Schultz, Daniel A. DiRocco, François Lévesque, Leo A. Joyce, Mikhail Reibarkh, Yining Ji, James F. Dropinski
Remotely oxygenated aliphatic amines represent an important class of synthetic building blocks to which there are currently no direct means of access. Reported here is an efficient and scalable solution that relies upon decatungstate photocatalysis under acidic conditions using either H2O2 or O2 as the terminal oxidant. Using these conditions a series of simple and unbiased aliphatic amine starting materials can be oxidized to value added ketone products. Lastly, in situ LED-irradiated NMR spectroscopy was utilized to monitor the kinetics of the reaction, enabling direct translation of the reaction in flow.

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

DOI: 10.1002/anie.201707537

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