Redox-neutral conversion of ubiquitous PV sources to a versatile PO2+ phosphorylation reagent

Schneider, Tobias; Schwedtmann, Kai; Fidelius, Jannis; Weigand, Jan J.

doi:10.1038/s44160-023-00344-0

Cited by 6 publications

(4 citation statements)

References 60 publications

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“…, where the tetrabutylammonium (TBA) salt was found to improve the solubility of the phosphate salt. Meanwhile， considered cyanuric chloride (TCT trichlorotriazine) with an amide were identified as the most costeffective reagents besides phosgene for activating alcohol and acid OH groups 46 . Herein, we develop a novel method for the conversion of phosphates to a versatile and practical phosphorylation reagent Furthermore, the resulting P(V)-reagent maintains the oxidation state of the phosphorus atom and serves as a valuable phosphorylation reagent for synthesizing a variety of organophosphate compounds.…”

Section: Inspired By Cummins's Previous Study On the Reduction Of [Tb...mentioning

confidence: 99%

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Cost-effective phosphates redox-neutral transformation to bench-stable phosphorylation precursor

Quan,

Tian,

Chen

et al. 2024

Preprint

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Modern synthesis methods of organophosphorus heavily rely on white phosphorus and its (oxy)chlorination reagents. Phosphates have the potential to serve as the perfect natural building blocks, forming the basis for organic and biochemical syntheses. However, poor solubility, high stability, and low reactivity make it challenging for transformation of phosphates to active reagents under mild conditions. Here we show an efficient conversion in which various phosphate sources are directly transformed into the [TBA][PO2X2] (X = Cl, F) phosphorylation reagents through a redox-neutral process by using cyanuric chloride and 1-formylpyrrolidine in the presence of a tetrabutylammonium chloride at ambient conditions. Key features of this conversion involve the utilization of cost-effective and readily available chemicals, circumventing the need of redox reactions with high-energy and forming a reactive yet stable P(V)-reagent. In comparison with the known phosphorylation precursor, [PO2X2]- salts are bench-stable, easy to handle, affording the phosphorylation compounds with before challenging substrates.

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Section: Inspired By Cummins's Previous Study On the Reduction Of [Tb...mentioning

confidence: 99%

“…Besides, limited approaches involve redox-neutral conversion of phosphates to P(V) chemicals through cleavage of the P-O bonds (methods e). More recently, Weigand and colleagues 46 achieved a breakthrough in converting P(V) sources into a PO 2+ phosphorylation reagent ((pyridine)2PO2[OTf]) (Fig. 1e).…”

Section: Introductionmentioning

confidence: 99%

Cost-effective phosphates redox-neutral transformation to bench-stable phosphorylation precursor

Quan,

Tian,

Chen

et al. 2024

Preprint

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“…13 To the best of our knowledge, the electrosynthesis of organophosphorus compounds using purely inorganic phosphorus building blocks has yet to be demonstrated. Of note, mild chemical pathways to convert PO 4 3− to C–P products 14 and C–P coupling of hypophosphites with alkenes 15 are emerging and another appealing direction yet are outside the scope of this work.…”

Section: Introductionmentioning

confidence: 99%

Dimethylphosphite electrosynthesis from inorganic phosphorus building blocks via oxidative coupling

Li,

Bemana,

Kornienko

2024

RSC Sustain.

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“…Therefore, the authors believe that the following areas deserve high priority of study in organophosphorus industry: The synthesis of (RO) 3 P/(RO) 2 P(O)H from P 4 and ROH The production of (RO) 3 P(O) from H 3 PO 4 and ROH The utilization of Ph 3 P(O) with a focus on restoring Ph 3 P using dihydrogen. …”

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confidence: 99%

Beyond Triphenylphosphine: Advances on the Utilization of Triphenylphosphine Oxide

Zhang,

Han

2024

J. Org. Chem.

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Triphenylphosphine oxide is a well-known industrial waste byproduct, and thousands of tons of it are generated every year. Due to its chemical stability and limited applications, settlement of this waste issue has drawn extensive attention from chemists. The reduction of triphenylphosphine oxide to triphenylphosphine is heretofore the most employed solution, and is well reviewed. In view of our recent studies on the selective and efficient conversion of Ph 3 P(O) to other valuable organophosphorus chemicals by using sodium, the present perspective mainly highlights the advances on the utilization of Ph 3 P(O) to prepare a diverse range of functional organophosphorus compounds, except Ph 3 P, via selective P−C, C−H, and P−O bond cleavages.P erhaps it is no longer necessary to emphasize the importance of organophosphorus compounds to our JOC readers. Today, they are common chemicals widely utilized in organic synthesis, catalysis, materials chemistry, agriculture, and pharmaceuticals, both in laboratory and industry settings. 1 However, there are numerous issues related to their preparation. In fact, so-called 'green methods,' by today's standards, are exceedingly rare for producing these compounds. The situation is particularly serious for the industry, where thousands of tons of organophosphorus compounds are manufactured each year using inefficient traditional methods that pose significant environmental, energy, and phosphorus resource challenges. 2

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Redox-neutral conversion of ubiquitous PV sources to a versatile PO2+ phosphorylation reagent

Abstract: Table of contents 1. General remarks, materials and methods .

Cited by 6 publications

References 60 publications

Cost-effective phosphates redox-neutral transformation to bench-stable phosphorylation precursor

Cost-effective phosphates redox-neutral transformation to bench-stable phosphorylation precursor

Dimethylphosphite electrosynthesis from inorganic phosphorus building blocks via oxidative coupling

Beyond Triphenylphosphine: Advances on the Utilization of Triphenylphosphine Oxide

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