Decarboxylative Bromooxidation of Indoles by a Vanadium Haloperoxidase

14 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Halooxindoles are versatile building blocks for the construction of complex oxindole-containing targets of biological importance. Despite their synthetic value, catalytic methods to synthesize 3-halooxindoles from readily available starting materials has remained undisclosed. We recently discovered that the chloroperoxidase from Curvularia inaequalis (CiVCPO) is a viable catalyst for the decarboxylative bromooxidation of 3-carboxyindoles to furnish 3-bromooxindoles with excellent regio- and chemoselectivity. In addition to the development of the synthetic method, this study provides evidence of a bromide recycling mechanism for the indole oxidation event. A discussion of the reaction development, substrate scope, mechanistic insights, and reaction applicability will be discussed herein.

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