Visible-Light-Induced, Catalyst-Free Radical Cross-Coupling Cyclization of N-Allylbromodifluoroacetamides with Disulfides or Diselenides

Zhi-Peng Ye; Peng-Ju Xia; Fang Liu; Yuan-Zhuo Hu; Dan Song; Jun-An Xiao; Ping Huang; Hao-Yue Xiang; Xiao-Qing Chen; Hua Yang

doi:10.1021/acs.joc.9b03490

Visible-Light-Induced, Catalyst-Free Radical Cross-Coupling Cyclization of N-Allylbromodifluoroacetamides with Disulfides or Diselenides

J Org Chem. 2020 Apr 17;85(8):5670-5682. doi: 10.1021/acs.joc.9b03490. Epub 2020 Apr 9.

Authors

Zhi-Peng Ye¹, Peng-Ju Xia¹, Fang Liu¹, Yuan-Zhuo Hu¹, Dan Song¹, Jun-An Xiao², Ping Huang³, Hao-Yue Xiang¹, Xiao-Qing Chen^{1

4}, Hua Yang^{1

4}

Affiliations

¹ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
² College of Chemistry and Materials Science, Guangxi Teachers Education University, Nanning, Guangxi 530001, P. R. China.
³ Technology Center of Hunan Provincial Tobacco Company, 386 Labor Middle Road, Changsha 410019, China.
⁴ Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety, Central South University, Changsha 410083, P. R. China.

PMID: 32240591
DOI: 10.1021/acs.joc.9b03490

Abstract

A visible-light-induced, catalyst-free radical cross-coupling cyclization of diselenides or disulfides with N-allylbromodifluoroacetamide has been developed. This developed protocol exhibits good functional group tolerance and affords a variety of 4-thio- and 4-seleno-substituted 3,3-difluoro-γ-lactams in moderate to good yields. Based on control experiments, a plausible radical-radical cross-coupling pathway is proposed.