Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 9, Pages 2199-2202Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805772
Keywords
2-pyridone; arenes; C-H activation; cyanation; palladium
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Funding
- Scripps Research Institute
- Bristol-Meyers Squibb
- NIH (NIGMS) [2R01GM084019]
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This article reports the first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (k(H)/k(D) =4.40) indicates that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.
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