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Synthesis of sulfoximines

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A dual nickel photocatalytic approach enables a scalable synthesis of a broad scope of N-arylated sulfoximines from the respective free NH-sulfoximines and bromoarenes. The reaction exhibits a high functional group tolerance. In addition, other sulfoximidoyl derivatives like sulfonimidamides and sulfinamides can smoothly be converted under the reaction conditions.
A. Wimmer, B. König, Org. Lett., 2019, 21, 2740-2744.


The use of copper(I) iodide and 4-DMAP achieves a N-arylation of sulfoximines with various arylboronic acids, including sterically substrates, in excellent yields at room temperature within a short span of time.
S. Gupta, S. Baranwal, N. Muniyappan, S. Sabiah, J. Kandasamy, Synthesis, 2019, 51, 2171-2182.


A simple and mild copper salt-catalyzed N-arylation of sulfoximines with aryl boronic acids is reported. The cross-couplings proceed without additional base at room temperature.
C. Moessner, C. Bolm, Org. Lett., 2005, 7, 2667-2669.


In a palladium-catalyzed cross-coupling strategy for the synthesis of various N-arylated sulfoximines, aryl bromides of variable substitution pattern were found to be effective coupling partners, whereas aryl iodides showed a nonpredictable behavior requiring lithium or silver salts as additives to ensure product formation in acceptable yields.
C. Bolm, J. P. Hildebrand, J. Org. Chem., 2000, 65, 169-175.


An efficient copper-TBAF-catalyzed arylation of sulfoximines with arylsiloxanes in dichloromethane at room temperature affords the desired N-aryl sulfoximines in good to excellent yields under an oxygen atmosphere. This mild C-N bond formation complements the existing approaches due to the advantageous properties of arylsiloxanes such as availability, low toxicity, ease of handling, high stability, and environmental benignity.
J. Kim, J. Ok, S. Kim, W. Choi, P. H. Lee, Org. Lett., 2014, 16, 4602-4603.


Two simple, inexpensive, and mild methods for copper-catalyed N-arylations of sulfoximines with aryl bromides and aryl iodides provide various N-arylated sulfoximines in high yields. These methods help to avoid the use of palladium catalysts or stoichiometric quantities of copper salts.
J. Sedelmeier, C. Bolm, J. Org. Chem., 2005, 70, 6904-6906.


J. Sedelmeier, C. Bolm, J. Org. Chem., 2005, 70, 6904-6906.


A general and direct N-arylation of sulfonamides and NH-sulfoximines by sodium arylsulfinates through a desulfitative pathway proceeded with catalytic loadings of Cu(II) without any external ligands. This arylation protocol offers high efficiency and good substituent tolerance.
Y. Jiang, Y. You, W. Dong, Z. Peng, Y. Zhang, D. An, J. Org. Chem., 2017, 82, 5810-5818.


A copper-catalyzed decarboxylative coupling of sulfoximines with aryl propiolic acids enables the preparation of N-alkynylated sulfoximines. Various substituents on both the sulfoximidoyl moiety as well as the aryl group of the propiolic acid were tolerated.
D. L. Priebbenow, P. Becker, C. Bolm, Org. Lett., 2013, 15, 6155-6157.


An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in good yields.
K. K. Rajbongshi, S. Ambala, T. Govender, H. G. Kruger, P. I. Arvidsson, T. Naicker, Synthesis, 2020, 52, 1279-1286.


In an efficient synthesis of N-aroylated sulfoximines, methylarenes serve as aroyl coupling partner of NH-sulfoximines in the presence of an environmentally benign iron catalyst. This protocol involves oxidation of benzylic C-H bonds of toluenes to generate aroyl radical intermediates followed by oxidative coupling with NH-sulfoximines. The intermediate aroyl radical is successfully trapped with TEMPO to prove the radical pathway of the reaction.
M. Muneeswara, S. S. Kotha, G. Sekar, Synthesis, 2016, 48, 1541-1549.


A method for the synthesis of N-aroylated sulfoximines involves a manganese oxide promoted C-H activation of methyl arenes to form an aroyl intermediate which then reacts readily with N-chlorosulfoximines to form a series of valuable aroyl sulfoximine derivatives in high yields.
D. L. Priebbenow, C. Bolm, Org. Lett., 2014, 16, 1650-1652.


A method for the synthesis of N-aroylated sulfoximines involves a manganese oxide promoted C-H activation of methyl arenes to form an aroyl intermediate which then reacts readily with N-chlorosulfoximines to form a series of valuable aroyl sulfoximine derivatives in high yields.
D. L. Priebbenow, C. Bolm, Org. Lett., 2014, 16, 1650-1652.