Photocatalytic Shono-type oxidation of N-alkylamides with hydrogen evolution
Keitaro Kato1, Shintaro Okumura1, Naoki Ishida1
1Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. ishida.naoki.5m@kyoto-u.ac.jp.
None:
A C-H alkoxylation reaction of N-alkylamides to N-acyl-N,O-acetals provides a straightforward and versatile method for functionalizing the α-position of amides. This reaction has been conventionally carried out by an electrochemical method (Shono oxidation). Although photoinduced variants are also known, they require sacrificial oxidants and/or the pre-functionalization of the amide substrates. We herein report a photoinduced reaction catalysed by an iridium photosensitizer and nickel bromide that eliminates the need for sacrificial oxidants and the pre-installation of reactive handles on the substrates.
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