Self-Catalyzed Phototandem Perfluoroalkylation/Cyclization of Unactivated Alkenes: Synthesis of Perfluoroalkyl-Substituted Quinazolinones

Bin Sun; Panyi Huang; Zhiyang Yan; Xiayue Shi; Xiaoli Tang; Jin Yang; Can Jin

doi:10.1021/acs.orglett.0c04225

Self-Catalyzed Phototandem Perfluoroalkylation/Cyclization of Unactivated Alkenes: Synthesis of Perfluoroalkyl-Substituted Quinazolinones

Org Lett. 2021 Feb 5;23(3):1026-1031. doi: 10.1021/acs.orglett.0c04225. Epub 2021 Jan 19.

Authors

Bin Sun¹, Panyi Huang², Zhiyang Yan¹, Xiayue Shi², Xiaoli Tang², Jin Yang², Can Jin^{1

2}

Affiliations

¹ Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P.R. China.
² College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P.R. China.

PMID: 33464096
DOI: 10.1021/acs.orglett.0c04225

Abstract

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (R_f = CF₃, C₃F₇, C₄F₉, C₆F₁₃, C₈F₁₇) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.