Synthesis of α,β-Unsaturated Phosphine Sulfides

Wang, Xianliang; Chen, Jinxiang; Jia, Xueshun; Yin, Liang

doi:10.1055/s-0039-1690685

Cited by 5 publications

(6 citation statements)

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“…THF, MeCN, DME, or toluene reaction produced phosphine sulfides (92) in about 20% yield. With DME as the solvent, the product yield rose (80%) as the reaction temperature was increased to 80 • C. The same trend was detected for the reaction in THF; product (92) was isolated in 96% yield at 80 • C. The product obtained was purified via chromatography using eluents EtOAc/hexane [97]. The designed reaction pathways enjoy a broad substrate scope.…”

Section: Synthesis Of Biologically Active N-alkylbenzisoselenazolthionessupporting

confidence: 53%

“…In 2013, Shibasaki and co-workers [96] reported the synthesis of asymmetric addition of dialkyl phosphite to N-thiophosphinoyl ketimines using copper(I)-catalyst to afford 90% to 96% yields. Recently, in the year 2019, Wang et al [97] envisioned the preparation of an array of α,β-unsaturated phosphine sulfides from the parent α,β-unsaturated phosphine oxides with Lawesson's reagent (Scheme 29). Due to the existence of conjugated enyne functionality, 1,4-thiazepines can be further expounded into more complex structures.…”

Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

“…The same trend was detected for the reaction in THF; product (92) was isolated in 96% yield at 80 °C. The product obtained was purified via chromatography using eluents EtOAc/hexane [97].…”

Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

“…LR, followed by the nucleophilic substitution of the obtained thioamides (96) with Li2Se2. Method B was built on the creation of benzisoselenazol-3-(2H)-ones (97) in the reaction of N-alkyl-o-iodobenzamides (94) with Li2Se2 and then the reaction of ebselen derivatives (97) with LR [99].…”

Section: Synthesis Of Biologically Active N-alkylbenzisoselenazolthionesmentioning

confidence: 99%

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A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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Lawesson’s reagent (LR) is a well-known classic example of a compound with unique construction and unusual chemical behavior, with a wide range of applications in synthetic organic chemistry. Its main functions were rounded for the thionation of various carbonyl groups in the early days, with exemplary results. However, the role of Lawesson’s reagent in synthesis has changed drastically, and now its use can help the chemistry community to understand innovative ideas. These include constructing biologically valuable heterocycles, coupling reactions, and the thionation of natural compounds. The ease of availability and the convenient usage of LR as a thionating agent made us compile a review on the new diverse applications on some common functional groups, such as ketones, esters, amides, alcohols, and carboxylic acids, with biological applications. Since the applications of LR are now diverse, we have also included some new classes of heterocycles such as thiazepines, phosphine sulfides, thiophenes, and organothiophosphorus compounds. Thionation of some biologically essential steroids and terpenoids has also been compiled. This review discusses the recent insights into and synthetic applications of this famous reagent from 2009 to January 2021.

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Section: Synthesis Of Biologically Active N-alkylbenzisoselenazolthionessupporting

confidence: 53%

Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

Section: Synthesis Of Biologically Active N-alkylbenzisoselenazolthionesmentioning

confidence: 99%

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A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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“…α,β‐Unsaturated phosphine sulfides 4 were prepared by treating α,β‐unsaturated phosphine oxides 3 with Lawesson's reagent . With 1 a and 4 a as the model substrates, the hydrophosphination was evaluated in the presence of a copper complex and Barton's base (Table ).…”

Section: Resultsmentioning

confidence: 99%

Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination

et al. 2020

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1,2‐Bisphosphines have been identified as one class of important and powerful chiral ligands in asymmetric catalysis with transition metals. Herein, a copper(I)‐catalyzed asymmetric hydrophosphination of α,β‐unsaturated phosphine sulfides was developed with the assistance of “soft–soft” interaction between copper(I)‐catalyst and the phosphine sulfide moiety, which afforded 1,2‐bisphosphine derivatives with diversified electronic nature and steric hindrance in high to excellent yields with high to excellent enantioselectivity. Moreover, the challenging catalytic asymmetric hydrophosphination/protonation reaction was achieved with excellent enantioselectivity. Strikingly, the dynamic kinetic resolution of racemic diarylphosphines was also successfully carried out with high to excellent diastereo‐ and enantioselectivities. Interestingly, the nucleophilic copper(I)‐diphenylphosphide species was characterized by 31P NMR spectrum and mass spectrum. At last, three products were transformed to chiral 1,2‐bisphosphines, which were employed as ligands in Rh‐catalyzed asymmetric hydrogenation of α‐amino‐α,β‐unsaturated ester. The α‐amino acid derivative was produced in high enantioselectivity, which demonstrated the utility of the present methodology.

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Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination

et al. 2020

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1,2-Bisphosphines have been identified as one class of important and powerfulc hiral ligands in asymmetric catalysis with transition metals.H erein, ac opper(I)-catalyzed asymmetric hydrophosphination of a,b-unsaturated phosphine sulfides was developed with the assistance of "soft-soft" interaction between copper(I)-catalyst and the phosphine sulfide moiety,w hich afforded 1,2-bisphosphine derivatives with diversified electronic nature and steric hindrance in high to excellent yields with high to excellent enantioselectivity. Moreover,the challenging catalytic asymmetric hydrophosphination/protonation reaction was achieved with excellent enantioselectivity.S trikingly,t he dynamic kinetic resolution of racemic diarylphosphines was also successfully carried out with high to excellent diastereo-and enantioselectivities. Interestingly,t he nucleophilic copper(I)-diphenylphosphide species was characterized by 31 PNMR spectrum and mass spectrum. At last, three products were transformed to chiral 1,2-bisphosphines,w hichw ere employed as ligands in Rhcatalyzeda symmetric hydrogenation of a-amino-a,b-unsaturated ester.The a-amino acid derivative was produced in high enantioselectivity,which demonstrated the utility of the present methodology.Scheme 1. Examples of reported chiral 1,2-bisphosphine ligands and working hypothesis to rapidly synthesize chiral 1,2-bisphosphine derivatives.Scheme 3. Application of synthesized chiral 1,2-bisphosphines in Rhcatalyzed asymmetric hydrogenation. Angewandte ChemieForschungsartikel 7127

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Synthesis of α,β-Unsaturated Phosphine Sulfides

Cited by 5 publications

References 1 publication

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination

Rapid Synthesis of Chiral 1,2‐Bisphosphine Derivatives through Copper(I)‐Catalyzed Asymmetric Conjugate Hydrophosphination

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