A One‐Pot Cascade Reaction by Combining NH‐Sulfoximines with Thiophenols Under Mild Conditions

Yao, Peng; Yang, Lin; Nie, Ruifang; Zheng, Yang; Liu, Yan-Zhao; Guo, Li; Wu, Yong

doi:10.1002/ejoc.201701643

Cited by 18 publications

(12 citation statements)

References 62 publications

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“…Wu and Guo described a metal‐catalyzed synthesis of N‐sulfenylsulfoximines by reacting NH‐sulfoximines and thiophenols. [90] In this process, the reaction proceeded with 2 equivalents of thiophenol and 20 mol% of [Cu(DMAP) 4 I]I as the catalyst at room temperature. A variety of NH‐sulfoximines and thiols were tested, and the methodology exhibited a very good functional group tolerance, providing moderate to good yields of the desired products 35 (Scheme 31 , b).…”

Section: Recent Developments In the Functionalization Of Nh‐sulfoximinesmentioning

confidence: 99%

Synthesis and Transformations of NH‐Sulfoximines

Andresini

Tota

Degennaro

et al. 2021

Chemistry A European J

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Section: Recent Developments In the Functionalization Of Nh‐sulfoximinesmentioning

confidence: 99%

Synthesis and Transformations of NH‐Sulfoximines

Andresini

Tota

Degennaro

et al. 2021

Chemistry A European J

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“…Later, Wu et al explored the catalytic activity of square pyramidal [Cu(DMAP) 4 I]I complex (Scheme 53) [69] and hexagonal Boron nitride (BN) supported copper(II) nanomaterial (Scheme 53) [70] towards the NÀ S bond formation of sulfoximines under ambient conditions. Both the protocols are effective to dispense the corresponding sulfenylated products 32 with wide range of functional group compatibility.…”

Section: Thioetherificationmentioning

confidence: 99%

N−H and C−H Functionalization of Sulfoximine: Recent Advancement and Prospects

2020

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Sulfoximine and its congeners are a versatile class of structural motifs widely found in a plethora of pharmaceutical compounds and crop protection industries due to their fascinating structural architecture. Former discoveries nicely demonstrates the synthetic routes of unmasked and various N-functionalized sulfoximines but recent efforts from the synthetic community have divulged the applicability of sulfoximine analogue as reusable and transformable DG (directing group) to fabricate multifunctionalized (Het)arenes and enhance the bioactivities. Considering the synthetic potentiality and great influence of this scaffold, we provide a summary of NÀ H/CÀ H functionalization strategies of sulfoximine and application (as a directing group) with special emphasis on the mechanistic underpinnings. Additionally, we also hoped that this comprehensive review article (up to midst of 2020) will be useful for synthetic researchers and medicinal chemists and will inspire for further novel chemical transformations in this arena.

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“…For N ‐thioetherification of sulfoximines 156 with thiols 157 , CuI/DMAP complex was also applied as a catalyst in the presence of oxygen (Scheme ) …”

Section: Synthesis Of Sulfoximines and Their Derivativesmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

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Oxidative strategies are a powerful tool in organic synthesis for the formation of heteroatom–heteroatom, carbon–heteroatom, and carbon–carbon bonds. Among these processes the reactions of oxidative S–N bond formation deserve considerable interest as convenient, effective, and environmentally friendly alternatives to existing methods for the synthesis of a great variety of organic compounds widely used in organic and medicinal chemistry. These transformations take place through the interaction of S‐ and N‐reagents and an oxidant, by radical or ionic mechanisms. Sulfinic acids and their salts, thiols, sulfonyl hydrazides, and thiosulfonates are generally used as S‐reagents; aliphatic and aromatic amines are usually applied as N‐reagents. The role of the oxidant mostly lies in the oxidation of the S‐reagent, after which the formed active species reacts with the N‐reagent to result in the S–N coupling product. There are two versions of oxidative S–N coupling processes: the intermolecular variant opens simple pathways to sulfen‐, sulfin‐, and sulfonamides, sulfenyl‐ and sulfoximines, sulfanes, and sulfur diimides, whereas the intramolecular one leads to the formation of various heterocycles. Of the major problems associated with successful performance of oxidative S–N coupling reactions, the first relates to the search for coupling partners that will work together to form a new bond under oxidative conditions. The second is the choice of a suitable oxidative system that will not overoxidize starting compounds. That is why mild oxidants, such as hypervalent iodine compounds and copper salts and complexes, are generally applied in these processes. This is the first exhaustive review relating to achievements in oxidative transformations involving S–N bond formation. It summarizes 134 references, mainly from 2000 to 2018, and is divided into chapters according to the classes of compounds synthesized.

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A One‐Pot Cascade Reaction by Combining NH‐Sulfoximines with Thiophenols Under Mild Conditions

Cited by 18 publications

References 62 publications

Synthesis and Transformations of NH‐Sulfoximines

Synthesis and Transformations of NH‐Sulfoximines

N−H and C−H Functionalization of Sulfoximine: Recent Advancement and Prospects

Oxidative Coupling with S–N Bond Formation

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