Synthesis of water-soluble phosphine oxides by Pd/C-catalyzed P-C coupling in water

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This patent describes a new, environmentally friendly method for synthesizing water-soluble phosphine oxides using palladium on carbon (Pd/C) as a catalyst to perform phosphorus-carbon (P-C) coupling reactions directly in water. The process avoids hazardous organic solvents, ligands, or additives, operates under mild conditions (including microwave-assisted heating), and allows easy product recovery and catalyst recycling. It is suitable for both small-scale laboratory work and large-scale industrial production.

Use CasesContent extracted from patent full text and abstract with AI.

• Production of water-soluble phosphine oxides as ligands in transition metal catalysis, especially for biphasic or water-based processes.
• Synthesis of intermediates for organocatalysis or pharmaceutical applications.
• Manufacturing catalysts for industrial processes such as the SHELL Higher Olefinic Process (SHOP) using water-soluble phosphines.
• Eco-friendly high-throughput synthesis of phosphine oxide derivatives in chemical and pharmaceutical industries.
• Scale-up production of functionalized phosphine oxides for use in materials science or chemical research.

BenefitsContent extracted from patent full text and abstract with AI.

• Enables a green, sustainable synthesis process by using water as the sole solvent and avoiding toxic organic solvents.
• Simple, fast, and high-yield method with broad substrate scope for different phosphorylated compounds.
• No need for external ligands or additives, reducing complexity and potential contamination.
• Microwave-assisted heating further reduces reaction times, increasing throughput and energy efficiency.
• Uses a recyclable heterogeneous catalyst (Pd/C), lowering costs and metal waste.
• Easy workup and product purification, suitable for both laboratory and industrial-scale application.
• Improved safety due to milder reaction conditions and use of air-stable reagents.

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Patent Abstract

Cross-coupling between diphenylphosphine oxide and halogenated benzoic acids catalyzed by Pd/C in water is a green, simple and fast protocol to obtain water-soluble tertiary phosphine oxides without the addition of ligands and additives. Low reaction times, microwave irradiation, and high substrate scope make this method general and excellent for lab- and large-scale synthesis without the need to use organic solvents for neither reaction nor workup.