I<sub>2</sub>‐Catalyzed Oxidative N−P Cross‐Coupling of Diarylphosphine Oxides and Sulfoximines

Tan, Mingchao; Zheng, Wenting; Yang, Lu; Zhou, Lihong; Zeng, Qingle

doi:10.1002/ajoc.201900476

Cited by 14 publications

(10 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[121] Based upon control experimental verifications and literature surveys, a reasonable mechanistic pathway was proposed. [121,122] The anionic form of sodium salt of aryl sulfinate 37.2 was subjected to molecular iodine to generate aryl sulfinyl radical 37.2 a which immediately transformed into its tautomeric form, aryl sulfonyl radical 37.2 b. This aryl sulfonyl radical 37.2 b went through a radical addition reaction with NH-sulfoximine deriva-…”

Section: Sà N Bond Forming Reactionsmentioning

confidence: 99%

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Samanta¹

2021

Asian J Org Chem

View full text Add to dashboard Cite

Transition metal‐catalyzed reactions are the heart of modern organic synthetic chemistry. In most cases, the synthesis of target molecules involved at least one or more transition metals such as palladium, ruthenium, rhodium, platinum, iridium, rhenium, cobalt, copper, iron, etc. But these transition metals are costly, toxic, and sometimes very difficult to separate from the target product. Instead of transition metals, molecular iodine or iodide salts have drawn the attention of modern organic synthetic chemists over a few decades due to their inexpensiveness, tolerance, and environmentally benign nature. So molecular iodine or iodide catalyzed reactions are highly efficient, atom‐economical, easy to control, eco‐ friendly protocol rather than transition metal‐catalyzed reactions. But many iodine‐catalyzed or mediated reactions, toxic solvents like tetrahydrofuran (THF), 1,4 dioxane, dimethylacetamide (DMA), dimethylformamide (DMF), benzene, toluene, chlorobenzene, nitrobenzene, n‐hexane, etc. are used which is a major concern in terms of environmental issues. Therefore, our present endeavour focuses on the recent developments (mainly in the period 2005–2020) of the iodine‐catalyzed or iodine‐mediated various reactions like oxidative additions, condensation reactions, C−C, C−N, C−O, C−S cross‐couplings etc. consciously performed in an aqueous medium to avoid environmental hazardous, which is a thrust area to the young researchers.

show abstract

Section: Sà N Bond Forming Reactionsmentioning

confidence: 99%

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Samanta¹

2021

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…N‐Phosphinyl sulfoximines were directly synthesized from sulfoximines and diarylphosphine oxides (Scheme 45). [78] …”

Section: Transformations Of Sulfoximinesmentioning

confidence: 99%

Syntheses and Transformations of Sulfoximines

Zheng

Chen

Feng

et al. 2020

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Sulfoximines are widely used as medicines, agricultural chemicals, chiral precursors, and chiral ligands in asymmetric synthesis, as well as pivotal intermediates for the construction of heterocyclic compounds. NH‐sulfoximines may be synthesized from thioethers, sulfoxides, sulfilimines, and sulfinamides. NH‐sulfoximines can undergo various transformations, such as arylations, alkylations, vinylations, and alkynylations. Here, we review the methods that have been applied to the syntheses and transformations of NH‐sulfoximines.

show abstract

“…As for the N‐phosphorylation of sulfoximines, in 2019, Jeyakumar group disclosed a Cu‐catalyzed dehydrogenative coupling between dialkylphosphate esters and sulfoximines [11] (Scheme 1f). Prabhu's group [12] and Zeng's group [13] (Scheme 1g) reported the cross‐coupling reactions of phosphine oxides with sulfoximines, respectively, using iodine and hydrogen peroxide. These approaches have enriched the synthetic routes for N−S/P substituted sulfoximine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Oxidative Dehydrogenative Coupling of Sulfoximines to Construct N‐sulfenyl and N‐phosphinyl Sulfoximines

Li,

Huang,

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Herein, an electrochemical oxidative approach for the synthesis of N‐sulfenyl and N‐phosphinyl sulfoximines has been established from readily available NH‐sulfoximines with thiophenols and diarylphosphine oxides. Utilizing the synergistic effect of halide salt and electrochemical oxidation, the desired products are obtained at room temperature in the absence of any acidic/basic/metallic additives.

show abstract

I₂‐Catalyzed Oxidative N−P Cross‐Coupling of Diarylphosphine Oxides and Sulfoximines

Cited by 14 publications

References 59 publications

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Syntheses and Transformations of Sulfoximines

Electrochemical Oxidative Dehydrogenative Coupling of Sulfoximines to Construct N‐sulfenyl and N‐phosphinyl Sulfoximines

Contact Info

Product

Resources

About

I2‐Catalyzed Oxidative N−P Cross‐Coupling of Diarylphosphine Oxides and Sulfoximines

Cited by 14 publications

References 59 publications

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Iodine‐Catalyzed or ‐Mediated Reactions in Aqueous Medium

Syntheses and Transformations of Sulfoximines

Electrochemical Oxidative Dehydrogenative Coupling of Sulfoximines to Construct N‐sulfenyl and N‐phosphinyl Sulfoximines

Contact Info

Product

Resources

About

I₂‐Catalyzed Oxidative N−P Cross‐Coupling of Diarylphosphine Oxides and Sulfoximines