Electrochemical Formation of N-Acyloxy Amidyl Radicals and Their Application: Regioselective Intramolecular Amination of sp2 and sp3 C–H Bonds

• DOI: 10.1021/acs.orglett.8b00981
• Publication Date: 2018-06-04T15:05:48Z
• Authors: Sheng Zhang; Lijun Li; Mengyu Xue; Ruike Zhang; Kun Xu; Chengchu Zeng
• Keywords: 01 natural sciences; 0104 chemical sciences

Electrochemical generation of N-acyloxy amidyl radicals via an inner-sphere electron-transfer process is described for the first time. With NaBr as the catalyst and electrolyte, the in situ generated amidyl radicals undergo intramolecular C(sp2/sp3)-H aminations to give lactams with unprecedented regio- and chemoselectivities. Moreover, the synthetic utility of current method is demonstrated by the synthesis of PJ34 and Phenaglaydon.