Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Metal- and O2-Free Oxidative C–C Bond Cleavage of Aromatic Aldehydes

Metal- and O2-Free Oxidative C–C Bond Cleavage of Aromatic Aldehydes
Kinthada Ramakumar, Stacey E. Brenner-Moyer, Guang Hu
An oxidative C–C cleavage of aldehydes requiring neither metals nor O2 was discovered. Homobenzylic aldehydes and α-substituted homobenzylic aldehydes were cleaved to benzylic aldehydes and ketones, respectively, using nitrosobenzene as an oxidant. This reaction is chemoselective for aromatic aldehydes, as an aliphatic aldehyde was unreactive under these conditions, and other reactive functionality such as ketones and free alcohols are tolerated. A mechanism accounting for the fate of the lost carbon is proposed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00784

DOI: 10.1021/acs.joc.7b00784

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