Trifluoromethylthiolation/Selenolation and Lactonization of 2-Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF3/SeCF3 Reagents

Haofeng Shi; Xingzong Wang; Xiaoxian Li; Beibei Zhang; Xuemin Li; Jingran Zhang; Jingyue Yang; Yunfei Du

doi:10.1021/acs.orglett.2c00563

Trifluoromethylthiolation/Selenolation and Lactonization of 2-Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF₃/SeCF₃ Reagents

Org Lett. 2022 Mar 25;24(11):2214-2219. doi: 10.1021/acs.orglett.2c00563. Epub 2022 Mar 14.

Authors

Haofeng Shi¹, Xingzong Wang^{2

3}, Xiaoxian Li¹, Beibei Zhang¹, Xuemin Li¹, Jingran Zhang¹, Jingyue Yang^{2

3}, Yunfei Du¹

Affiliations

¹ Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
² Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, China.
³ Nano-biotechnology Key Lab of Hebei Province, Yanshan University, Qinhuangdao 066004, China.

PMID: 35285237
DOI: 10.1021/acs.orglett.2c00563

Abstract

The combined use of BnS(O)CF₃/BnSe(O)CF₃ with Tf₂O as SCF₃/SeCF₃ reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/trifluoromethylseleno)isocoumarins from 2-alkynylbenzoates. The mechanistic pathway was postulated to involve formation of the electrophilic SCF₃/SeCF₃ species via interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Indicators and Reagents
Molecular Structure
Safrole / analogs & derivatives
Selenium*
Sulfoxides*

Substances

Indicators and Reagents
Sulfoxides
Selenium
Safrole
sulfoxide