Related references
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Article
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Jessica T. T. Liu et al.
Summary: A robust and general method for the preparation of N-acylsulfenamides is reported, which are important functionalities for the asymmetric synthesis of high oxidation state sulfur compounds. This straightforward transformation involves the reaction of various compounds with stable N-thiosuccinimides or N- thiophthalimides, which can be prepared in a single step from commercial thiols. The use of stable reactants eliminates the need for highly reactive sulfenyl chlorides.
SYNTHESIS-STUTTGART
(2023)
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Xianda Wu et al.
Summary: A novel and efficient method for the synthesis of sulfilimines has been developed using diaryliodonium salts for the S-arylation of sulfenamides. The reaction proceeds smoothly under transition-metal-free and air conditions, resulting in good to excellent yields of sulfilimines via selective S-C bond formation. This scalable protocol exhibits a broad substrate scope, good functional group tolerance, and excellent chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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Gao-feng Yang et al.
Summary: In this study, a tandem oxidative/nucleophilic substitution approach for the synthesis of sulfinamidines was developed. The reaction, enabled by N-bromosuccinimide (NBS) as an oxidant and various readily available amines as nucleophiles, achieved high yields (up to 98%) without the need for any additives or catalysts. This method offers the advantages of being time-efficient, safe, easy to scale up, and compatible with diverse functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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Andrew T. Champlin et al.
Summary: Sulfur alkylation of N-acyl sulfenamides with alkyl halides leads to sulfilimines, with yields ranging from 47% to 98%. This reaction demonstrates a wide scope with different aryl and alkyl sulfenamides, as well as various N-acyl groups. Alkyl halides with different steric and electronic properties, including methyl, primary, secondary benzyl, and propargyl halides, are effective reactants. Furthermore, an asymmetric phase-transfer alkylation was successfully demonstrated. The resulting sulfilimine products can be easily converted to N-acyl and free sulfoximine, which are important motifs in medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
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Qingjin Liang et al.
Summary: This article describes an unprecedented synthetic route to sulfilimines through a copper catalyzed Chan-Lam-type coupling reaction of sulfenamides. The key to success is the chemoselective S-arylation of S(II) sulfenamides to form S(IV) sulfilimines, which overrides the competitive and thermodynamically favored C-N bond formation. The selectivity is achieved through a selective transmetallation event where bidentate sulfenamide coordination promotes the S-arylation pathway. The mild and environmentally friendly catalytic conditions allow for a wide range of functional group compatibility, enabling the efficient preparation of various diaryl or alkyl aryl sulfilimines.
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(2023)
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Gao-feng Yang et al.
Summary: Desymmetrizing enantioselective hydrolysis of in situ-generated symmetric aza-dichlorosulfonium from sulfenamides allows for the preparation of chiral sulfonimidoyl chlorides, which serve as a general stable synthon for obtaining a series of chiral S(VI) derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Guoling Huang et al.
Summary: In this study, a metal-free and redox-neutral strategy was developed for the selective S-alkylation of sulfenamides under basic conditions to yield sulfilimines. The key step involves the resonance between bivalent nitrogen-centered anions, generated after deprotonation of sulfenamides under alkaline conditions, and sulfinimidoyl anions. Our sustainable and efficient approach employs sulfur-selective alkylation of readily accessible sulfenamides and commercially available hydrocarbons, leading to the successful synthesis of 60 sulfilimines in high yields (36-99%) and short reaction times.
Article
Chemistry, Organic
Xunbo Lu et al.
Summary: In this study, a novel and efficient approach for the oxidative esterification of sulfenamides using phenyliodonium diacetate is presented. The method enables the synthesis of sulfinimidate esters and sulfilimines under mild and metal-free conditions, with yields up to 99%. The protocol is scalable and compatible with a diverse range of substrates and functional groups, showing potential for late-stage functionalization of pharmacologically relevant molecules. Furthermore, a plausible reaction mechanism is proposed to explain the observed sequence of events.
Article
Chemistry, Organic
Nathaniel S. Greenwood et al.
Summary: This study reports the sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides using inexpensive copper(I) iodide as the catalyst. The reaction inputs include both aryl and alkyl sulfenamides and highly sterically hindered aryl and 5- and 6-membered ring heteroaryl iodides. The study also discloses the (hetero)arylation of S-methyl sulfenamides, including complex aryl iodides, and the Smiles rearrangement of electron-deficient S-heteroaryl sulfilimines.
Article
Chemistry, Organic
Qinglong Zhou et al.
Summary: This article presents a practical and efficient base-mediated sulfur arylation reaction for the preparation of sulfilimines. By using various N-acyl and N-aryl sulfenamides, and diaryliodonium salts as reactants, the sulfilimines can be obtained in high yields with excellent chemoselectivities.
Article
Chemistry, Organic
Jonathan A. Ellman et al.
Summary: Sulfur-arylation of sulfenamides via a Chan-Lam-type coupling with boronic acids is reported, leading to the formation of sulfilimines. A broad range of aryl and alkyl sulfenamides and boronic acids were used as reactants. The utility of this reaction was demonstrated by introducing sulfilimines into approved drugs and accessing medicinally relevant sulfoximines and sulfondiimines through derivatization of sulfilimine products.
Article
Chemistry, Organic
Guoling Huang et al.
Summary: A transition-metal-free and redox-neutral synthesis of sulfilimines was achieved through the S-arylation of readily obtainable sulfenamides using diaryliodonium salts. The key step involved resonance between bivalent nitrogen-centered anions, leading to the deprotonation of sulfenamides under alkaline conditions and subsequent formation of sulfinimidoyl anions. Experimental results showed that sulfinimidoyl anionic species acted as effective nucleophilic reagents, providing sulfilimines with high yields and excellent chemoselectivity in a transition-metal-free protocol and under mild conditions.
Article
Chemistry, Organic
Yue Chen et al.
Summary: A mild and simplified method for preparing sulfilimines via selective S-C bond formation instead of traditional S-N bond formation is developed. This method is attractive because it uses readily available alkyl bromide or alkyl iodide as alkylation reagents, water as solvent, is easy to perform, and convenient for late-stage diversification of drugs.
Article
Chemistry, Organic
Guoling Huang et al.
Summary: In this study, a novel and efficient method for the oxidativeamination reaction of sulfenamides was developed using diacetoxyiodobenzene and amines under basic conditions. This technique simplifies the synthesis of sulfinamidines, achieving high yields up to 99% without the need for metal catalysts. Possible reaction pathways were proposed to explain the observed molecular sequence of events. This cutting-edge approach not only advances the synthesis of valuable sulfinamidine compounds, but also expands the synthetic toolbox available to chemists, paving the way for future discoveries in organic synthesis and potential applications in medicinal chemistry.
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(2023)
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Pei Xie et al.
Summary: A facile and efficient method for the synthesis of sulfilimines through multicomponent reaction of arynes, sulfamides, and thiosulfonates was developed. This protocol showed good compatibility with structurally diverse substrates and functional groups, providing the corresponding sulfilimines in high yields. Mechanism studies revealed the key role of sulfenamide in the reaction.
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Yifeng Guo et al.
Article
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Xianda Wu et al.
Summary: An efficient and metal-free approach for the synthesis of sulfilimines from sulfenamides with aryne and cyclohexyne precursors has been developed. The reaction proceeds through unusual S-C bond formation, offering a novel and practical entry to access a wide range of sulfilimines in moderate to good yields with excellent chemoselectivity. Moreover, this protocol is amenable to gram-scale synthesis and applicable to the transformation of the products into useful sulfoximines.
Article
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Longjun Ma et al.
Summary: This article describes a catalytic asymmetric synthesis method for N-acyl sulfinamides, using N-acyl sulfenamides as substrates and achieving high yields and enantioselectivities by forming efficient hydrogen bonds with chiral phosphoric acid, which can be easily converted to sulfoxides without loss of enantioselectivity.
Article
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(2022)
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Ziqian Bai et al.
Summary: This study reports a method for the synthesis of N-acyl sulfenamides via copper-catalyzed S-amidation of thiols with dioxazolones. This method is efficient, convenient, and broadly applicable. The resulting N-acetyl sulfenamides can be used as highly effective S-sulfenylation reagents and enable the synthesis of sterically demanding disulfides that are difficult to prepare by other means.
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(2022)
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Yu Han et al.
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