O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo- or Thermal-Induced N-O Cleavage in C(sp2)-C(sp3) Bond Formation

Peng-Ju Xia; Yuan-Zhuo Hu; Zhi-Peng Ye; Xu-Jie Li; Hao-Yue Xiang; Hua Yang

doi:10.1021/acs.joc.9b03251

O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo- or Thermal-Induced N-O Cleavage in C(sp²)-C(sp³) Bond Formation

J Org Chem. 2020 Mar 6;85(5):3538-3547. doi: 10.1021/acs.joc.9b03251. Epub 2020 Feb 4.

Authors

Peng-Ju Xia¹, Yuan-Zhuo Hu¹, Zhi-Peng Ye¹, Xu-Jie Li¹, Hao-Yue Xiang¹, Hua Yang^{1

2}

Affiliations

¹ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
² Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety, Central South University, Changsha 410083, P. R. China.

PMID: 31971800
DOI: 10.1021/acs.joc.9b03251

Abstract

O-Perfluoropyridin-4-yl group was first installed onto cycloketone oximes as a new electrophore, which was proven to be efficient iminyl radical precursors under photocatalytic and thermal conditions. A range of O-perfluoropyridin-4-yl oximes were successfully utilized in C(sp²)-C(sp³) bond formations of quinoxalin-2(1H)-ones and alkenes, providing facile accesses to a range of functionalized alkylnitriles.