Specific 1,2‐Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β‐Ketonitriles

作者：Zhanhui Yang, Kwon‐Il Son, Siqi Li, Bing‐Nan Zhou, Jiaxi Xu · 发表于：European Journal of Organic Chemistry · 年份：2014 · DOI：10.1002/ejoc.201402901 · 被引用次数：31 · 研究领域：Cyclopropane Reaction Mechanisms、Asymmetric Synthesis and Catalysis、Synthesis and Biological Evaluation

Abstract A series of β‐ketonitriles was synthesized within 30 min under mild conditions through the BF 3 · OEt 2 ‐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, γ,δ‐unsaturated β‐ketonitriles are also accessible by this method by using cinnamaldehydes.