Synthesis of Oxindoles through the Gold-Catalyzed Oxidation of N-Arylynamides

α‐Oxo gold carbenoids generated by the oxidation of N‐arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N‐oxide works as the oxidant, ligand, and base in this transformation. A mild and conven...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-05, Vol.2013 (14), p.2775-2779
Main Authors: Yang, Liu-Qing, Wang, Kai-Bing, Li, Chuan-Ying
Format: Article
Language:English
Subjects:
Alkynes
Carbenes
Gold
Heterocycles
Oxidation
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Summary:α‐Oxo gold carbenoids generated by the oxidation of N‐arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N‐oxide works as the oxidant, ligand, and base in this transformation. A mild and convenient gold‐catalyzed method to synthesize functionalized oxindoles by using N‐arylynamides has been developed. A gold carbenoid was proven to be the key intermediate, which underwent a Friedel–Crafts‐type reaction to afford the oxindoles.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300162