Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 29, Pages 6380-6384Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402901
Keywords
Synthetic methods; Nucleophilic addition; Hydride shift; Ketonitriles; Aldehydes; Diazo compounds
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Funding
- National Basic Research Program of China [2013CB328905]
- National Natural Science Foundation of China (NSFC) [21172017, 21372025]
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A series of beta-ketonitriles was synthesized within 30 min under mild conditions through the BF3 center dot OEt2-catalyzed addition reactions of diazoacetonitrile to aromatic aldehydes and subsequent 1,2-hydride shift. This method is advantageous in that it is operationally simple, mild and metal-free conditions are used, the substrate scope is wide, and the products are obtained in moderate to high yields (up to 81%). Additionally, gamma, delta-unsaturated beta-ketonitriles are also accessible by this method by using cinnamaldehydes.
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