10.1021/acs.oprd.9b00403.s001 Anne-Laure Barthelemy Anne-Laure Barthelemy Victor Certal Victor Certal Guillaume Dagousset Guillaume Dagousset Elsa Anselmi Elsa Anselmi Luc Bertin Luc Bertin Laurence Fabien Laurence Fabien Bruno Salgues Bruno Salgues Philippe Courtes Philippe Courtes Christian Poma Christian Poma Youssef El-Ahmad Youssef El-Ahmad Emmanuel Magnier Emmanuel Magnier Optimization and Gram-Scale Preparation of <i>S</i>‑Trifluoromethyl Sulfoximines and Sulfilimino Iminiums, Powerful Reagents for the Late Stage Introduction of the CF<sub>3</sub> Group American Chemical Society 2019 Sulfilimino Iminiums CF 3 group 40 g reappraisal adaptation article crude mixtures purification synthese trifluoromethyl sulfilimino iminiums Stage Introduction Powerful Reagents late-stage introduction methodology electrophilic reagent Optimization compound trifluoromethyl sulfilimino iminium 5 sulfoximine 4 DSC measurements 30 g CF 3 Group S Gram-Scale Preparation Trifluoromethyl sulfoximines Sulfoximine 2019-11-08 22:44:23 Journal contribution https://acs.figshare.com/articles/journal_contribution/Optimization_and_Gram-Scale_Preparation_of_i_S_i_Trifluoromethyl_Sulfoximines_and_Sulfilimino_Iminiums_Powerful_Reagents_for_the_Late_Stage_Introduction_of_the_CF_sub_3_sub_Group/10278053 <i>S</i>-Trifluoromethyl sulfoximines and <i>S</i>-trifluoromethyl sulfilimino iminiums are important reagents for the electrophilic or radical late-stage introduction of the CF<sub>3</sub> 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 <b>4</b> and 40 g of <i>S</i>-trifluoromethyl sulfilimino iminium <b>5</b> 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.