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Published March 3, 2017 | Supplemental Material
Journal Article Open

Oxidative Fragmentations and Skeletal Rearrangements of Oxindole Derivatives


An oxidative sequence for the conversion of oxindoles to structurally distinct heterocyclic scaffolds and aniline derivatives is disclosed by the combination of a copper-catalyzed C–H peroxidation and subsequent base-mediated fragmentation reaction. In contrast to classic enzymatic (i.e., kynurenine pathway) and biomimetic methods (i.e., Witkop–Winterfeldt oxidation) for oxidative indole cleavage, this protocol allows for the incorporation of external nucleophiles. The new transformation displays broad functional group tolerance and is applicable to tryptophan derivatives, opening potential new avenues for postsynthetic modification of polypeptides, bioconjugation, and unnatural amino acid synthesis.

Additional Information

© 2017 American Chemical Society. Received: December 20, 2016; Published: February 14, 2017. This work was supported by the NSF under the CCI Center for Selective C–H Functionalization (CHE-1205646). We thank DAAD (postdoctoral fellowship to H.F.T.K.), NSERC (graduate scholarship to A.F.G.G.), NSF (predoctoral research fellowship to D.C.D., No. DGE-1144469), the Gordon and Betty Moore Foundation, Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Larry Henling (Caltech) is acknowledged for X-ray analysis, and Dr. Robert Craig and Dr. Guillaume Lapointe (both Caltech) are thanked for helpful discussions. The authors declare no competing financial interest.

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