Application of pentacoordinated spirophosphorane as a new organocatalyst for the Michael addition reaction

Wang, Peipei; Li, Wanjiao; Han, Kehui; Guo, Yating; Zhao, Yufen; Cao, Shuting

doi:10.1080/10426507.2021.1946062

Cited by 6 publications

(3 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13 C {1H} NMR (76 MHz, CDCl 3 ): δ 167.7, 167.0, 159.6, 129.3, 128.1, 114.4, 78.0, 62.2, 62.0, 55.4, 55.2, 42.5, 14.1, 13.9. NMR spectra are in agreement with the literature data 60.…”

supporting

confidence: 91%

Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

et al. 2022

View full text Add to dashboard Cite

Nowadays, design of the new chiral ligands for organometallic catalysts is often based on the step-by-step increase in their complexity to improve efficiency. Herein we describe that simple in situ addition of the fluoride source to the asymmetric organometallic catalyst can improve not only activity but also enantioselectivity. Bromide−nickel diimine complexes were found to catalyze asymmetric Michael addition in low yields and ee, but activation with fluoride leads to a significant improvement in catalyst performance. The developed approach was applied to prepare several enantioenriched GABA analogues.

show abstract

“…13 C {1H} NMR (76 MHz, CDCl 3 ): δ 167.7, 167.0, 159.6, 129.3, 128.1, 114.4, 78.0, 62.2, 62.0, 55.4, 55.2, 42.5, 14.1, 13.9. NMR spectra are in agreement with the literature data 60.…”

supporting

confidence: 91%

Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Our group has been working on the synthesis and chemical properties of pentacoordinate AA-HSPs for nearly 20 years, , and we devote ourselves to exploring the diversity of the reaction of pentacoordinate AA-HSPs as precursors. Over the past several decades, the synthetic methods for constructing P–Se/P–S skeletons using tetracoordinate phosphorus compounds have attracted a great deal of attention from synthetic chemists.…”

Section: Introductionmentioning

confidence: 99%

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

Zhang,

Guo,

Zhao

et al. 2024

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

The NaOAc-assisted aerobic oxidation reaction of pentacoordinate hydrospirophosphoranes and dichalcogenyl compounds with open air as a green oxidant has been developed under mild conditions. A series of novel pentacoordinate spirophosphoranes with P–Se/P–S bonds were synthesized in excellent yields. The reaction mechanism was determined by 31P nuclear magnetic resonance tracing experiments, high-resolution mass spectrometry tracing experiments, and X-ray diffraction analysis. The method features a broad substrate scope, good functional group tolerance, and a high degree of atomic utilization and is meaningful for the synthesis of bioactive chalcogenphosphate compounds with chalcogen and phosphorus moieties.

show abstract

“…[8] Furthermore, our group found that pentacoordinate spirophosphorane was a type of potential organocatalyst to catalyze organic reactions. [25] The addition reactions of olefins and tricoordinate or tetracoordinate phosphorus compounds bearing PÀ H bond have been reported. [26][27][28][29][30] However, to the best of our knowledge, there is few report on the direct pentacoordinate PÀ C formation through the hydrophosphorylation reaction of olefins.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and Electron‐Deficient Alkenes Catalyzed by Organic Phosphine

et al. 2021

Self Cite

View full text Add to dashboard Cite

PR3 efficiently catalyzes the addition of H‐spirophosphorane to electron‐deficient alkenes to give the spirophosphoranes with a pentacoordinate P−C bond in moderate to excellent yields. This practical procedure was conducted by using PR3 as an organocatalyst, which avoided the use of an additional base, traditional heating, and metal reagents. The investigation of the reaction mechanism showed that the zwitterion intermediate served as the base to further catalyze hydrospirophosphorane. Then the spirophosphoranide formed as a nucleophile attacked electron‐deficient alkene to give the addition products. This reaction is a first and simple hydrophosphorylation reaction of alkenes to construct pentacoordinate P−C bond under organocatalysis

show abstract

Application of pentacoordinated spirophosphorane as a new organocatalyst for the Michael addition reaction

Cited by 6 publications

References 32 publications

Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and Electron‐Deficient Alkenes Catalyzed by Organic Phosphine

Contact Info

Product

Resources

About