Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4390-4. doi: 10.1002/anie.201400938. Epub 2014 Mar 18.
A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3 ⋅OEt2 . After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide.
开发了一种使用乙烯基叠氮化物作为亲核试剂合成含酰胺分子的方法，该亲核试剂对碳亲电试剂（如亚胺、醛和醇在 BF3 ⋅OEt2 存在下生成的碳正离子）具有反应活性。乙烯基叠氮化物进行亲核进攻后，生成的亚胺重氮离子中间体的取代基迁移，形成腈鎓离子，该离子经水解得到相应的酰胺。
