Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes

Zhi-Long Lei; Tai-Chen Liu; Fei-Hu Cui; Ying-Ming Pan; Shu-Hui Li; Hai-Tao Tang

doi:10.1021/acs.orglett.3c02143

Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes

Org Lett. 2023 Aug 18;25(32):6001-6005. doi: 10.1021/acs.orglett.3c02143. Epub 2023 Aug 7.

Authors

Zhi-Long Lei¹, Tai-Chen Liu¹, Fei-Hu Cui¹, Ying-Ming Pan¹, Shu-Hui Li¹, Hai-Tao Tang¹

Affiliation

¹ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China.

PMID: 37548921
DOI: 10.1021/acs.orglett.3c02143

Abstract

An electrochemical facilitated three-component trifluoromethylation/spirocyclization reaction of N-(arylsulfonyl)acrylamides, CF₃SO₂Na, and H₂O has been developed. Without the requirement of chemical oxidants, a number of unexplored trifluoromethylated 4-azaspiro[4.5]decanes were obtained in satisfactory yields under mild conditions. This work provides a new synthetic strategy for fluorine-containing spirocyclic compounds and shows a new perspective for the reactivity study of N-(arylsulfonyl)acrylamides.