Copper-Catalyzed Multicomponent Reactions of Intramolecular and Intermolecular Thiotrifluoromethylation of Alkenes: Access to CF3-Containing 2-Iminothiazolidines and Isothioureas

Sainan Liu; Liqin Jiang

doi:10.1021/acs.orglett.2c02854

Copper-Catalyzed Multicomponent Reactions of Intramolecular and Intermolecular Thiotrifluoromethylation of Alkenes: Access to CF₃-Containing 2-Iminothiazolidines and Isothioureas

Org Lett. 2022 Oct 7;24(39):7157-7162. doi: 10.1021/acs.orglett.2c02854. Epub 2022 Sep 27.

Authors

Sainan Liu¹, Liqin Jiang¹

Affiliation

¹ School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China.

PMID: 36166662
DOI: 10.1021/acs.orglett.2c02854

Abstract

A copper-catalyzed multicomponent reaction of secondary amines bearing allyl substitution, isothiocyanates, and Togni reagent II has been developed under Cs₂CO₃ in DCE at 75 °C. An intermolecular multicomponent reaction of thioureas, activated and unactivated alkenes, and Togni reagent II has also been developed under DMAP in acetonitrile at room temperature. These two alkene difunctionalization reactions provide CF₃-containing 2-iminothiazolindines and isothioureas in moderate to excellent yields with broad substrate scope and good functional group tolerance, respectively.