Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 20, Pages 11288-11294Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02085
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- Elsevier
- South African National Research Foundation [NRF/95404]
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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-theart (>100 degrees 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.
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