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

Adduct-catalyzed tandem electro-thermal synthesis of organophosphorus (III) compounds from white phosphorus DOI Creative Commons

Jingcheng Hu,

Haoyu He,

Minghao Xu

et al.

National Science Review, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

Electrooxidation strategies for synthesizing readily oxidizable products face notable challenges, especially when the oxidation potential of is lower than that reactants or high current densities are necessary. The electrooxidation synthesis trivalent organophosphorus compounds (OPCs (III)) from white phosphorus (P4) has demonstrated but hindered by selectivity issues due to over-oxidation. Herein, we report a tandem electro-thermal pathway addresses these challenges in producing OPCs (III) P4. process begins with an step generates stable transfer reagent, then thermochemically converted into various high-value (III). Utilizing hexafluoroisopropanol (HFIP) as nucleophile and optimizing tetrabutylammonium iodide (TBAI)-4-dimethylaminopyridine (DMAP)-adduct catalytic system, developed efficient electrophilic reagent via electrosynthesis. adduct facilitates P4 enhances nucleophilicity HFIP, thereby improving process. This approach supports density, scales up hundred-gram level without yield loss, remains compatible fluctuating green electricity.

Language: Английский

Citations

3
Ternary Photoredox/Nickel/Halide Catalysis for the Phosphorylation of Alcohols with White Phosphorus DOI

Ziman Cai,

Yumeng Zhang,

Yidan Cao

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(12), P. 8330 - 8335

Published: June 8, 2023

Dialkyl phosphites (DAPIs) are important precursors in the formation of phosphorus–carbon and phosphorus–heteroatom bonds with significant industrial applications. Traditional PCl3-based procedures suffer from high waste production toxic reaction conditions. The direct conversion white phosphorus (P4) to DAPIs can circumvent these issues by avoiding use Cl2 PCl3. We present a waste-free, environmentally friendly approach for synthesizing using P4 alcohols, leveraging combination photoredox catalyst, nickel halide anion. This photocatalytic method enables efficient coupling various alcohols. Advantageously, this is also suitable synthesis trialkyl phosphates triaryl phosphorotrithioates.

Language: Английский

Citations

23
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
Metal-free visible-light-induced phosphorylation of unactivated alkyl iodides with white phosphorus as the P-atom source DOI
Fushan Chen,

Jialiang Peng,

Yue Ying

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(17), P. 6629 - 6634

Published: Jan. 1, 2023

This is the first organic-dye-catalyzed alkylation of white phosphorus with unactivated alkyl iodides to afford dialkylphosphines.

Language: Английский

Citations

11
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
Bridging Homogeneous and Heterogeneous Catalysis: Ni@CPOL-dppp&PPh3-Catalyzed Symmetric H-Phosphonate Diester Synthesis from Sodium Hypophosphite DOI
Jin Yang,

Dang‐Wei Qian,

Hongli Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7912 - 7918

Published: April 29, 2025

Language: Английский

Citations

0
Beyond Triphenylphosphine: Advances on the Utilization of Triphenylphosphine Oxide DOI
Jianqiu Zhang, Li‐Biao Han

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2090 - 2103

Published: Jan. 25, 2024

Triphenylphosphine oxide is a well-known industrial waste byproduct, and thousands of tons it are generated every year. Due to its chemical stability limited applications, settlement this issue has drawn extensive attention from chemists. The reduction triphenylphosphine heretofore the most employed solution, well reviewed. In view our recent studies on selective efficient conversion Ph

Language: Английский

Citations

3
A Convenient Mass Spectrometry Platform for Differential Analysis of N-Glycans and Potential Biomarker Discovery from Muscle Aging Models Using 15n/14n-Phosphonium-Hydrazide Labelling Strategy DOI
Qianru Ma, Yanqing Li,

Jiecheng Lu

et al.

Published: Jan. 1, 2024

Language: Английский

Citations

0
Catalytic Activation of Bis(2,2,2‐trifluoroethyl) Phosphite with Hf(IV) for the Synthesis of Mixed Dialkyl Phosphites DOI Creative Commons
Dario Mrdović,

Yuki Saito,

Shū Kobayashi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 21, 2024

Abstract We developed a second generation of Lewis acid catalyst enabling selective and user‐friendly phosphonylation diverse alcohols. This one‐pot method utilizes P(III) reagent bis(2,2,2–trifluoroethyl) phosphite under mild conditions. Exploring the influence metal selection in catalysts revealed four highly active complexes for alcohol phosphonylation: Zn(II), Al(III), Zr(IV), Hf(IV). Notably, Hf(IV) displayed superior selectivity compared to previously Zn(II) catalyst.

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