Electrochemical cyclization ofN-cyanamide alkenes with CF3SO2Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds

Yan, Zhihua; Li, Weicheng; Wu, Yuheng; Yan, Qi-Bo; Wei, Zhonglin; Liao, Wei‐Wei

doi:10.1039/d2qo01323a

Cited by 7 publications

(2 citation statements)

References 65 publications

(22 reference statements)

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“…Despite the reagent diversity, the predominant utilization of anodic oxidation with CF 3 SO 2 Na has prevailed, albeit fraught with intricate, environmentally burdensome, and impure synthetic protocols. [ 18 ] Thus, the pursuit of more sustainable and economically viable alternatives remains a critical imperative to augment the trifluoromethylation toolkit. [ 19 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

Ge,

Qiao,

Zhang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryA novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF3+OTf−) for trifluoromethylation of imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis of TT–CF3+OTf− without the requirement of external oxidants or catalysts, aligning with the principles of green chemistry. A wide range of imidazole‐fused heteroaromatic compounds including imidazo[1,2‐a]pyridines and benzo[d]imidazo[2,1‐b]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility with various functional groups and a broad substrate scope. Moreover, the method's applicability for one‐pot sequential reactions enables the reduction of waste and resource consumption by eliminating the need for intermediate purification steps.

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Section: Background and Originality Contentmentioning

confidence: 99%

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

Ge,

Qiao,

Zhang

et al. 2024

Chin. J. Chem.

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“…6 Several electro-oxidative and electro-reductive trifluoromethyl radical generations followed by addition to heterocycles, and alkene difunctionalization have been reported using Langlois reagent, (CF 3 SO 2 ) 2 Zn and CF 3 SO 2 Cl, respectively (Scheme 1a). 7 Notably, most of these methods are associated with the use of various acids and transition metals like Mn, Y, Mg, etc. 8…”

mentioning

confidence: 99%

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

et al. 2023

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Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl‐Oxindoles

He,

Mei,

Escorihuela

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryA novel electrochemical multicomponent cascade reaction of indole‐tethered alkenes with CF3SO2Na and n‐Bu4NI has been developed, which enables the rapid assembly of spiropyrrolidinyl‐oxindoles in good yields. The experimental results and DFT calculations suggest that this reaction proceeds through the oxidation of CF3SO2Na, radical coupling with alkene, spirocyclization, oxidation of sulfinate, iodide substitution, and water coupling. This strategy features mild reaction conditions, easy‐to‐handle reactants, and good chemical yields. This finding not only enriches the research contents of indole‐tethered alkenes but also provides a green strategy for the construction of spiropyrrolidinyl‐oxindoles compared with the existing methodologies.

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Electrochemical cyclization ofN-cyanamide alkenes with CF₃SO₂Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds

Abstract: An electrochemical (bis)trifluoromethylative cyclization of N-cyanamide alkenes and alkynes was described, in which commercially available CF3SO2Na and readily available starting materials engaged in a novel electrochemical and sustainable process to...

Cited by 7 publications

References 65 publications

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

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

Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl‐Oxindoles

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