- Copper-catalyzed imination of sulfoxides and sulfides
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Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
- Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
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supporting information
p. 4697 - 4702
(2019/07/22)
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- Palladium-Catalyzed Direct α-Arylation of p -Methoxybenzyl-Protected S, S -Dimethylsulfoximine
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Sulfoximines have recently gained considerable recognition as an important structural motif in the life sciences. This is especially true for (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, such as the marketed insecticide sulfoxaflor, as well as the clinical candidates PTEFb inhibitor BAY 1143572 and ATR inhibitor AZD 6738 for the treatment of cancer. Herein, the first palladium-catalyzed direct α-arylation of p-methoxybenzyl-protected S,S-dimethylsulfoximine using readily available (hetero)aryl bromides is reported. This new method provides a safe, short, and efficient approach to (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, an important class of bioactive compounds, demonstrated by application of this methodology to an improved synthesis of PTEFb inhibitor BAY 1143572.
- Sirvent, Juan A.,Bierer, Donald,Webster, Robert,Lücking, Ulrich
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p. 1024 - 1036
(2017/03/10)
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- General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor
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The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clinical candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesising a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, commercially available precursor is discussed.
- Goldberg, Frederick W.,Kettle, Jason G.,Xiong, Jian,Lin, Daoguang
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p. 6613 - 6622
(2015/03/30)
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- PEROXYACETIC ACID: A USEFUL COOXIDANT FOR THE RUTHENIUM TETROXIDE OXIDATION OF N-SULFONYLSULFILIMINES
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The oxidation of a wide variety of N-sulfonylsulfilimines to the corresponding sulfoximines is described.The oxidation involves the use of peroxyacetic acid as a cooxidant for the actual oxidant, ruthenium tetroxide, in a biphasic media.
- Ketcha, Daniel M.,Swern, Daniel
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p. 915 - 920
(2007/10/02)
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- COPPER CATALYZED REACTIONS OF S,S-DIARYL-N-TOSYLSULFILIMINES WITH SULFOXIDES: NEW SYNTHESIS OF N-TOSYLSULFOXIMINES
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S,S-Diaryl-N-tosylsulfilimines were readily reduced by treatment with copper to give the corresponding sulfides and a copper-tosylnitrenoid-complex which upon reacting with sulfoxides afforded the corresponding N-tosylsulfoximines, derived from sulfoxides in fair yields.When optically active (-)-(S)-methylphenyl sulfoxide was used, the corresponding (+)-N-tosylsulfoximine was obtained together with the sulfide derived from the N-tosylsulfilimine.The stereochemical course of the conversion of (-)-(S)-sulfoxide to (+)-N-tosylsulfoximine was found to be mainly retention (76percent) with partial racemization due to thermal pyramidal inversion of the starting sulfoxide.
- Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
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p. 213 - 222
(2007/10/02)
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- A CONVENIENT PREPARATION OF N-(ARENESULFONYL)SULFOXIMINES BY OXIDATION OF N-(ARENESULFONYL)SULFILIMINES WITH SODIUM HYPOCHLORITE IN A TWO PHASE SYSTEM
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N-(Arenesulfonyl)sulfilimines can be oxidized to the corresponding sulfoximines in high yields with sodium hypochlorite in an AcOEt-H2O two phase system in the presence of quaternary ammonium salts as catalysts.
- Furukawa, Naomichi,Akutagawa, Kunihiko,Yoshimura, Toshiaki,Oae, Shigeru
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p. 3989 - 3992
(2007/10/02)
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