New Frontiers in Phosphorothioate Formation: Harnessing Inorganic Phosphorus Sources DOI
Jiawei He,

Xuesi Zhou,

Zixuan Wan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14691 - 14702

Published: Jan. 1, 2024

This review highlights the latest advancements in synthesis of phosphorothioates and their derivatives from inorganic phosphorus sources, focusing on applicability, mechanisms, current limitations, potential future directions.

Language: Английский

Recent progress on the functionalization of white phosphorus in China DOI Creative Commons
Xinlei Huangfu, Zhongzhen Wang, Yu Chen

et al.

National Science Review, Journal Year: 2024, Volume and Issue: 11(6)

Published: May 2, 2024

Direct synthesis of organophosphorus compounds from white phosphorus represents a significant but challenging subject, especially in the context ongoing efforts to comprehensively improve phosphorus-derived chemical industry driven by sustainability and safety concerns. China is world's largest producer phosphorus, creating demand for green transformation this crucial feedstock. This review provides an overview advancements activation Chinese research teams, focusing on direct construction P‒C/N/O/S/M bonds phosphorus. Additionally, we offer some insights into prospective directions future. paper aims attract more researchers engage area, stimulating follow-up exploration fostering enduring advances.

Language: Английский

Citations

11
Photocatalytic C–P bond formation based on the reaction of carbon-centered radicals with phosphides DOI

Shiyi Zhao,

Yi-Yun Huang,

Shihao Deng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4882 - 4894

Published: Jan. 1, 2024

This review focuses on the synthesis of C–P bonds using carbon-centered radicals with phosphorous compounds different valence states (P III , P V 4 ) under photocatalysis.

Language: Английский

Citations

6
Water mediated synthesis of dialkylphosphine oxides from white phosphorus and N-(acyloxy)phthalimides DOI Creative Commons
Guo Tang, Xinyu Zhu,

Jiali He

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The first water mediated synthesis of dialkylphosphine oxides and α-hydroxy phosphine from P 4 without a chlorination step oxidation process is presented.

Language: Английский

Citations

0
Direct conversion of various phosphate sources to a versatile P-X reagent [TBA][PO2X2] via redox-neutral halogenation DOI Creative Commons

Yaling Tian,

Dongping Chen,

Yao Chai

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 26, 2025

Abstract Inorganic phosphates hold significant potential as ideal natural building blocks, forming a fundamental basis for organic and biochemical synthesis. However, their limited solubility, inherent chemical stability, low reactivity pose substantial challenges to converting into organophosphates under mild conditions. This study introduces an efficient method the direct conversion of P(V)-X reagents, [TBA][PO 2 X ] (X = Cl, F), via redox-neutral halogenation process. utilizes cyanuric chloride (or fluoride) reagent, in combination with 1-formylpyrrolidine tetrabutylammonium (TBAC), ambient The approach enables effective various P(V) sources, including orthophosphates, pyrophosphoric acid, Na 3 P O 9 5 . Furthermore, we demonstrate synthetic utility P(V)-Cl reagent phosphorylation diverse -, S N - C- nucleophiles. Key advantages this process include use inexpensive readily available chemicals, avoidance high-energy redox reactions, generation reactive yet stable reagent.

Language: Английский

Citations

0
Straightforward Superbase-Mediated Reductive O-Phosphorylation of Aromatic and Heteroaromatic Ketones with Red Phosphorus in the Superbase Suspension KOH/DMSO(H2O) DOI Creative Commons
Vladimir A. Kuimov, Svetlana F. Malysheva, Nataliya A. Belogorlova

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1367 - 1367

Published: March 18, 2025

It was shown for the first time that diaryl(hetaryl)ketones are capable of directly phosphorylating with red phosphorus in superbase suspension KOH/DMSO(H2O) at 85 °C 1.5 h to afford potassium bis(diaryl(hetaryl)methyl)phosphates were earlier inaccessible a yield up 45%. The ESR data demonstrate unlike previously published phosphorylation elemental phosphorus, this new reaction proceeds via single electron transfer from polyphospide anions diaryl(hetaryl)ketones. This is example C-O-P bond generation during strongly basic media, which usually provides C-P formation.

Language: Английский

Citations

0
Direct Synthesis of Phosphoryltriacetates from White Phosphorus via Visible Light Catalysis DOI Open Access
Yu Chen, Wei Liu, Xinlei Huangfu

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(7)

Published: Nov. 6, 2023

Organophosphorus compounds (OPCs) are widely used in many fields. However, traditional synthetic routes the industry usually involve multistep and hazardous procedures. Therefore, it's of great significance to construct such an environmentally-friendly facile way. Herein, a photoredox catalytic method has been developed novel phosphoryltriacetates. Using fac-Ir(ppy)

Language: Английский

Citations

7
Selective Functionalization of White Phosphorus with Alkyl Bromides under Photocatalytic Conditions: A Chlorine-Free Protocol to Dialkyl and Trialkyl Phosphine Oxides DOI

Jialiang Peng,

An Wang, Yan Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9316 - 9321

Published: Oct. 24, 2024

A novel and efficient method for the direct selective alkylation of white phosphorus (P4) with alkyl bromides has been developed, utilizing 4DPAIPN as photocatalyst Hantzsch ester reductant. This facilitates synthesis structurally diverse dialkyl phosphine oxides in good yields, offering a streamlined alternative to traditional stepwise approach chlorinating P4 Cl2 subsequently displacing chlorine atom. Noteworthy features this reaction include excellent product selectivity, remarkable functional group tolerance, broad substrate scope. Additionally, is effective trialkyl oxides.

Language: Английский

Citations

1
Recent Advances in the Synthesis of Commercially Available Phosphite Antioxidants DOI Creative Commons

Yuliang Zhu,

Xinyue Liu,

Ying Zhong Tang

et al.

ChemistryOpen, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract Phosphite antioxidants exhibit superior anti‐aging and color‐stabilizing properties when incorporated into polymer materials. Their synergistic antioxidative effects are particularly noteworthy used in combination with hindered phenol other primary antioxidants, serving as effective secondary displaying antioxidation effects. This review systematically classifies the synthetic methods for phosphite three distinct categories based on types of starting materials: synthesis from phosphorus trichloride, phosphorus‐containing esters, white phosphorus. Additionally, it delineates reaction mechanisms associated these approaches provides an overview future potential research directions applications organophosphorus antioxidants.

Language: Английский

Citations

1
Cost-effective phosphates redox-neutral transformation to bench-stable phosphorylation precursor DOI Creative Commons
Zheng‐Jun Quan,

Yaling Tian,

Dongping Chen

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: June 20, 2024

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

Language: Английский

Citations

0
Closing the Loop: Low‐Waste Phosphorus Functionalization Enabled by Simple Disulfides DOI Creative Commons
Thomas M. Horsley Downie, Ajdin Velić, Laís Vanessa Sousa Coelho

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Useful monophosphorus products are obtained from both white and red phosphorus via a simple strategy involving initial oxidation by aryl disulfides followed quenching with nucleophiles. Direct transformations of elemental usually very challenging, forcing chemists to instead rely on inefficient hazardous multi‐step methods. However, here they achieved using inexpensive easy‐to‐handle reagents, providing access diverse P−C, P−N P−O bonded in good yields. By isolating the thiolate byproducts these reactions, simple, closed loop can be that produces only minimal, benign waste byproducts, contrast other direct This even elaborated into true (electro)catalytic cycle, which is extremely rare field functionalization.

Language: Английский

Citations

0