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Optimization and Gram-Scale Preparation of S‑Trifluoromethyl Sulfoximines and Sulfilimino Iminiums, Powerful Reagents for the Late Stage Introduction of the CF3 Group

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journal contribution
posted on 08.11.2019, 22:44 by Anne-Laure Barthelemy, Victor Certal, Guillaume Dagousset, Elsa Anselmi, Luc Bertin, Laurence Fabien, Bruno Salgues, Philippe Courtes, Christian Poma, Youssef El-Ahmad, Emmanuel Magnier
S-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.