op9b00403_si_001.pdf (506.88 kB)
Optimization and Gram-Scale Preparation of S‑Trifluoromethyl Sulfoximines and Sulfilimino Iminiums, Powerful Reagents for the Late Stage Introduction of the CF3 Group
journal contribution
posted on 2019-11-08, 22:44 authored by Anne-Laure Barthelemy, Victor Certal, Guillaume Dagousset, Elsa Anselmi, Luc Bertin, Laurence Fabien, Bruno Salgues, Philippe Courtes, Christian Poma, Youssef El-Ahmad, Emmanuel MagnierS-Trifluoromethyl sulfoximines and S-trifluoromethyl
sulfilimino iminiums are important reagents for
the electrophilic or radical late-stage introduction of the CF3 group. We disclose in this article a reappraisal of our previous
methodologies and their adaptation to a large scale. More than 30
g of the key sulfoximine 4 and 40 g of S-trifluoromethyl sulfilimino iminium 5 are prepared
without purification. DSC measurements have been performed on both
the crude mixtures and the isolated compounds in order to ensure a
safe process. The costs of the syntheses are also detailed and discussed.
History
Usage metrics
Categories
Keywords
Sulfilimino IminiumsCF 3 group40 greappraisaladaptationarticlecrude mixturespurificationsynthesetrifluoromethyl sulfilimino iminiumsStage IntroductionPowerful Reagentslate-stage introductionmethodologyelectrophilicreagentOptimizationcompoundtrifluoromethyl sulfilimino iminium 5sulfoximine 4DSC measurements30 gCF 3 Group SGram-Scale PreparationTrifluoromethyl sulfoximinesSulfoximine
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC