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A Low-Temperature, Transition Metal-Free Cross Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles

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JournalThe Journal of organic chemistry
DatePublished - 19 Sep 2017
Number of pages22
Pages (from-to)1-22
Original languageEnglish

Abstract

A new low-temperature procedure for the synthesis of 3,3-disubstituted 2-oxindoles via cross dehydrogenative coupling (CDC) is reported. The use of a strong, non-reversible base in these reactions has been found to effect a dramatic drop in reaction temperature (to room temperature) relative to the current state-of-the-art (>100 °C). When employing iodine as an 'oxidant', new evidence suggests that this transformation may occur via a transiently stable iodinated intermediate rather than by direct single-electron oxidation.

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© 2017 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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