Synthesis of Trifluoromethylated γ-Lactams through Radical Cascades of N-Cyano Alkenes with CF₃SO₂Na

Abstract

We report herein a facile strategy to synthesize trifluoromethylated γ-lactams through trifluoromethylcarbonylation of N-cyano alkenes using readily available CF 3 SO 2 Na as the CF 3 radical source. A range of trifluoromethyl-containing γ-lactams was obtained in good yields. This transition-metal-free protocol is demonstrated with mild conditions, broad substrate scope, good functional group tolerance, convenient reagents, and an easy-to-handle operating system.

Langlois Reagent: An Efficient Trifluoromethylation Reagent

“…The Methodology provides a broad substrate scope with various substituted substrates, good functional group tolerance, and easy scalability. 16 In summary, Langlois' reagent is an efficient trifluoromethylating or fluoroalkylating reagent with diverse functionalization, a broad substrate scope, and ease of handling due to its solid nature, among other fluorinating agents. Recently, much attention has been paid to this reagent as the -CF3 incorporated organic compounds, which display a variety of applications in several areas of chemistry.…”

Photocatalytic Cyclization Cascades by Radical Relay toward Pyrrolo[1,2-a]indoles: Synthesis, Mechanism, and Application

“…Considering the biological and functional activities of organic compounds significantly influenced by the trifluoromethyl group, various methodologies for the preparation of trifluoromethylated organic compounds have been developed in the past decades. − Notably, Langlois’ reagent (CF 3 SO 2 Na) has generally been used in the field of radical chemistry, probably due to its high stability, commercial availability, and lower-cost. − Prompted by these related publications and our previous work, − we envisioned that a series of trifluoromethylated pyrrolo­[1,2- a ]­indoles could be prepared from the oxidative cyclization cascade of unactivated N -alkene-linked indoles with CF 3 SO 2 Na by a photocatalytic trifluoromethyl radical relay (Scheme ). Hopefully, this paper was also highlighted by gaining insights into reaction mechanisms through DFT-based calculation and application exploration in living-cell imaging.…”

Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines

“…2 Various transition metal-catalyzed, photocatalyzed and mediator-driven trifluoromethylations have been reported previously to construct the C–CF 3 bond. 3 Nevertheless, green and proficient methods for incorporating a trifluoromethyl group into valuable organic scaffolds are still urgently required.…”