- 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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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
- Barthelemy, Anne-Laure,Certal, Victor,Dagousset, Guillaume,Anselmi, Elsa,Bertin, Luc,Fabien, Laurence,Salgues, Bruno,Courtes, Philippe,Poma, Christian,El-Ahmad, Youssef,Magnier, Emmanuel
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p. 704 - 712
(2019/11/19)
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- One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides
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A general efficient one-pot synthesis of S-perfluoroalkylated NH-sulfoximines from sulfides has been developed using phenyliodine diacetate (PIDA) and ammonium carbamate. Remarkable rate enhancement with trifluoroethanol was observed, presumably due to H-bonding effects. These mild and metal-free conditions are compatible with -CH2F, -CFCl2, -CF2H, -CF2Br, -C4F9, and -CF3 groups, in both the alkyl- and aryl series. Based on a 19F NMR analysis, a λ6-acetoxysulfanenitrile intermediate was proposed.
- Chaabouni, Slim,Lohier, Jean-Fran?ois,Barthelemy, Anne-Laure,Glachet, Thomas,Anselmi, Elsa,Dagousset, Guillaume,Diter, Patrick,Pégot, Bruce,Magnier, Emmanuel,Reboul, Vincent
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supporting information
p. 17006 - 17010
(2018/10/31)
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- Functionalized S-perfluorinated sulfoximines: Preparation and evaluation in catalytic processes
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N-substituted S-perfluoroalkylated sulfoximines were synthesized from the NH sulfoximines either by a copper coupling reaction with aryl halides or by a reaction with electrophilic substrates. The procedure allowed the preparation of N,N′-bridged bis sulf
- Le, Thanh-Nghi,Diter, Patrick,Pégot, Bruce,Bournaud, Chloée,Toffano, Martial,Guillot, Regis,Vo-Thanh, Giang,Yagupolskii, Yurii,Magnier, Emmanuel
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p. 179 - 187
(2015/11/10)
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- A mild and efficient procedure for the N-functionalization of S-perfluoroalkylated aryl sulfoximines
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N-Acylated perfluoroalkylated sulfoximines are synthesized easily from the corresponding free NH-sulfoximines on reaction with acid chlorides. This mild procedure is extended to diacid chlorides for the preparation of dimeric N-bridged sulfoximines and to reactions with chloroformates, carbamoyl chlorides, chlorothio-noformates and thiocarbamoyl chlorides as electrophiles. Georg Thieme Verlag Stuttgart New York.
- Mace, Yohan,Constant-Urban, Celine,Bouvet, Sebastien,Pegot, Bruce,Bournaud, Chloee,Toffano, Martial,Vo-Thanh, Giang,Diter, Patrick,Magnier, Emmanuel
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p. 1505 - 1512
(2013/07/05)
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- Sulfoximines as a versatile scaffold for electrophilic fluoroalkylating reagents
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New electrophilic fluoroalkylating agents based on the sulfoximine skeleton as a common platform are described. We demonstrate the importance of the activating group, attached to the nitrogen, and its specificity for the fluorinated group to be delivered.
- Urban, Celine,Cadoret, Frederic,Blazejewski, Jean-Claude,Magnier, Emmanuel
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experimental part
p. 4862 - 4867
(2011/10/09)
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- Sulfilimines and sulfoximines by reaction of nitriles with perfluoroalkyl sulfoxides
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The species obtained by activation of perfluoroalkylated sulfoxides with trifluoromethanesulfonic anhydride behaves as highly electrophilic entities. Their reaction with nitriles allows a Ritter-like process leading to the new fluorinated acylsulfilimines
- Mace, Yohan,Urban, Celine,Pradet, Charlotte,Marrot, Jerome,Blazejewski, Jean-Claude,Magnier, Emmanuel
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supporting information; experimental part
p. 3150 - 3153
(2009/12/07)
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