Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles.
| Autor: | Donald JR; Department of Chemistry, University of York , Heslington, York YO10 5DD, U.K., Taylor RJK; Department of Chemistry, University of York , Heslington, York YO10 5DD, U.K., Petersen WF; Department of Chemistry, University of York , Heslington, York YO10 5DD, U.K. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2017 Oct 20; Vol. 82 (20), pp. 11288-11294. Date of Electronic Publication: 2017 Sep 28. |
| DOI: | 10.1021/acs.joc.7b02085 |
| Abstrakt: | 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, nonreversible 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) procedure. 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. |
| Databáze: | MEDLINE |
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