- Rhodium(III)-Catalyzed C?H Alkynylation of N-Methylsulfoximines
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A rhodium(III)-catalyzed direct C?H alkynylation of a wide range of N-methylsulfoximines with (bromoethynyl)triisopropylsilane has been developed. This protocol is compatible with both (S,S)-diaryl sulfoximines and (S,S)-alkyl aryl sulfoximines, and shows mild conditions, and good functional group tolerance. The synthetic utility of this method has been demonstrated by subsequent various transformations of the products.
- Wang, Tao,Wang, Yi-Ning,Wang, Rui,Wang, Xi-Sheng
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p. 2449 - 2452
(2018/08/17)
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- N - methylation of the sulfoxide of imine derivative (by machine translation)
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A simple, clean and high-effective synthetic method of a novel N-methylated sulfoximine derivative is provided in the invention. The invention relates to the fields of pesticides, organic chemical engineering and fine chemical engineering. The method essentially is an organic synthesis reaction that a methyl free radical, which is generated from peroxides, and a sulfoximine compound are subjected to free radical coupling to form new C-N bonds. The method includes the step of carrying out a reaction to obtain the N-methylated sulfoximine derivative in a common organic solvent under a heating condition from the raw materials including diphenyl sulfoximine and a methylating reagent (peroxides) under the catalysis by copper. The method is 2-20 h in reaction time under a heating and stirring condition. The molar ratio of the raw materials is that the diphenyl sulfoximine to the methylating reagent is 1:0.5-3.0. The raw materials are reacted under the heating condition and then reaction products are subjected to simple after treatments to obtain the N-methylated sulfoximine derivative at a yield being 36-87%. The invention develops a series of N-methylating methods based on a free radical process to prepare a series of N-methylated sulfoximine derivatives. The method is simple in operation and after treatments, and is simple and practical in synthesis of these compounds.
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Paragraph 0043-0044
(2018/04/01)
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- Copper promoted: N -alkylation of sulfoximines with alkylboronic acid under mild conditions
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The copper meditated N-methylation of sulfoximines using methylboronic acid is reported. The reactions provide excellent yields in a short span of time under mild conditions. The optimized conditions were also found to be suitable for the N-alkylation of sulfoximine with different alkylboronic acids. In addition, N-methylation and cyclopropylation of the bioactive l-methionine sulfoximine derivative was demonstrated under standard reaction conditions.
- Gupta, Surabhi,Chaudhary, Priyanka,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 8493 - 8498
(2017/10/27)
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- Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms
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Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to α-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like products. With X=SO2Ph, the major product was the corresponding α,α-dichloroalkyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations.
- Saleh, Basil A.,Smith, Keith,Elliott, Mark C.,Jones, D. Heulyn,Kariuki, Benson M.,El Hiti, Gamal A.
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p. 6914 - 6928
(2016/10/14)
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- Copper-catalyzed N-methylation/ethylation of sulfoximines
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A protocol for the copper-catalyzed N-methylation of sulfoximines with di-tert-butyl peroxide (DTBP) was developed. This protocol has good functional group tolerance leading to N-methylated sulfoximines in moderate to good yields. Besides, N-ethylation of sulfoximines was achieved in the presence of bis(1,1-dimethylpropyl)peroxide as the ethylating agent under a standard procedure.
- Teng, Fan,Cheng, Jiang,Yu, Jin-Tao
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supporting information
p. 9934 - 9937
(2015/10/12)
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- Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
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As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
- Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
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p. 5594 - 5602
(2015/09/01)
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- Direct Access to N -Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure
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Synthetically relevant N-alkyl-substituted sulfoximines are directly prepared from sulfides by an unprecedented one-pot imidation/oxidation sequence. In situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the corresponding N-alkylsulfoximines. In this manner, gram quantities of the products can be obtained in a short period of time avoiding the use of toxic and cumbersome to handle alkylating reagents.
- Dannenberg, Carl Albrecht,Bizet, Vincent,Bolm, Carsten
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supporting information
p. 1951 - 1959
(2015/06/30)
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- Photocycloaddition of biscyclopropyl alkenes to C60: An unprecedented approach toward cis-1 tricyclic-fused fullerenes
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A novel, simple, and entirely regioselective tandem cycloaddition of biscyclopropyl-substituted alkenes to [60]fullerene has been revealed. This reaction affords cis-1 tricyclic-fused organofullerenes bearing the hitherto elusive 5-4-5 fused tricyclic ring system.
- Tzirakis, Manolis D.,Alberti, Mariza N.,Orfanopoulos, Michael
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supporting information; experimental part
p. 3364 - 3367
(2011/09/12)
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- Synthesis of phosphanyl sulfoximines through phospha-michael reaction of alkenyl sulfoximines and their evaluation as chiral bidentate 1, 5-N, P ligands for palladium in asymmetric allylic alkylation
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The intermolecular phospha-Michael reaction of cyclic and acyclic alkenyl sulfoximines proceeds readily and yields the corresponding phosphanyl sulfoximines in good yield. The asymmetric induction provided, by sulfoximine group in C-P bond formation is ap
- Lemasson, Fabien,Gais, Hans-Joachim,Runsink, Jan,Raabe, Gerhard
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scheme or table
p. 2157 - 2175
(2010/06/16)
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