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

James R Donald; Richard John Kenneth Taylor; Wade F Petersen

doi:10.1021/acs.joc.7b02085

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

James R Donald, Richard John Kenneth Taylor, Wade F Petersen

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1-22
Number of pages	22
Journal	The Journal of organic chemistry
DOIs	https://doi.org/10.1021/acs.joc.7b02085
Publication status	Published - 19 Sept 2017

Bibliographical note

© 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.

Keywords

Journal Article

Access to Document

10.1021/acs.joc.7b02085

acs.joc.7b02085
© 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.
Accepted author manuscript, 484 KB

Cite this

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