Lewis acid-assisted N-fluorobenzenesulfonimide-based electrophilic fluorine catalysis in Beckmann rearrangement. Issue 51 (21st December 2016)

• Record Type: Journal Article
• Authors: Xie, Fukai; Du, Chuan; Pang, Yadong; Lian, Xu; Xue, Chentao; Chen, Yanyu; Wang, Xuefei; Cheng, Maosheng; Guo, Chun; Lin, Bin; Liu, Yongxiang
• Is Part Of: Tetrahedron letters. Volume 57:Issue 51(2016)
• Page Start: 5820
• Page End: 5824
• Publication Date: 2016-12-21
• Subjects: N-Fluorobenzenesulfonimide -- Beckmann rearrangement -- Lewis acid assistance -- Electrophilic fluorine catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.054
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A Lewis acids-assisted NFSI-catalyzed Beckmann rearrangement is described firstly. The chelation between Lewis acid and NFSI is responsible for the mechanism. A number of Lewis acids can be used to activate the NFSI to catalyze reactions. Control experiments and DFT calculations help to prove the mechanism. Abstract: A microwave-assisted N- fluorobenzenesulfonimide (NFSI)/Lewis acid-catalyzed Beckmann rearrangement was developed. The remarkable promotion to the electrophilicity of NFSI by Lewis acids was illustrated utilizing a series of readily available oxime substrates. The action model between NFSI and Lewis acids was probed by control experiments and theoretical calculations.