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Usage

Uses

Used in Organic Chemistry:
(E)-(4-fluorostyryl)diphenylphosphine oxide is used as a ligand in metal-catalyzed reactions for its ability to enhance the efficiency and selectivity of these reactions. Its unique structure allows it to form stable complexes with metals, facilitating various chemical transformations.
Used in Materials Chemistry:
In the field of materials chemistry, (E)-(4-fluorostyryl)diphenylphosphine oxide is utilized in the fabrication of organic semiconductor materials. Its electronic properties and structural features make it a promising candidate for the development of advanced materials with improved performance in electronic devices.
Used in Optoelectronic Devices:
(E)-(4-fluorostyryl)diphenylphosphine oxide is also investigated for its photophysical properties, which make it a potential component in the development of optoelectronic devices. Its ability to interact with light and its electronic properties contribute to its potential use in creating more efficient and advanced optoelectronic systems.
Used in Catalytic Processes:
(E)-(4-fluorostyryl)diphenylphosphine oxide is employed as a valuable component in the development of new catalytic processes. Its unique structure and properties enable it to improve the performance of catalysts, leading to more effective and environmentally friendly chemical reactions.

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 4559-70-0 Diphenylphosphine oxide 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 100-58-3 phenylmagnesium bromide 
• 1831-63-6 diphenylphosphorylacetic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 405-99-2 para-fluorostyrene 
• 706-06-9 3-(4-flurophenyl)prop-2-ynoic acid 
• 459-32-5 4-fluorocinnamic acid 

Relevant academic research and scientific papers

Knoevenagel Condensation of Phosphinoylacetic Acids with Aldehydes: An Efficient One-Pot Strategy for the Synthesis of P-Functionalized Alkenyl Compounds

A wide range of commercially available aldehydes have been applied to Knoevenagel condensation reaction to give E -alkenylphosphine oxides and vinylphosphine oxides. The readily available phosphinoylacetic acids derived from P(O)-H compounds were used as the starting materials in the reaction, providing a highly stereoselective and efficient method for constructing α,β-unsaturated phosphine oxides. Moreover, this simple and practical procedure provides an alternative and more environmentally friendly synthesis strategy for this type of P-functionalized alkenyl compounds.

Ceric(IV) Ammonium Nitrate Mediated Phosphorylation of Alkenes: Easy Access to (E)-Vinylphosphonates

An inexpensive Ceric(IV) ammonium nitrate mediated phosphorylation of alkenes has been developed. Without adding expensive metals and other additives, various (E)-alkenylphosphane oxides are obtained through an easy route in a one-pot manner. Preliminary

Cobaloxime Catalysis: selective synthesis of alkenylphosphine oxides under visible light

Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- A nd stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).

Cobaloxime Catalysis: Selective Synthesis of Alkenylphosphine Oxides under Visible Light

Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- and stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).

Transition-metal-free C-P bond formation via decarboxylative phosphorylation of cinnamic acids with P(O)H compounds

A novel, transition-metal-free phosphorylation of cinnamic acids with P(O)H compounds has been developed via radical-promoted decarboxylation under mild conditions. This method provides simple, efficient, and versatile access to valuable (E)-alkenylphosphine oxides in satisfactory yields with a wide variety of substrates.

Preparation method of alkenyl diphenylphosphine compound

The invention discloses a preparation method of an alkenyl diphenylphosphine compound. The method adopts a derivative of aryl ethylene and diphenylphosphine oxide as initial raw materials, under the protection of nitrogen, ceric ammonium nitrate is also added, a molar ratio of the derivative of aryl ethylene to diphenylphosphine oxide to ceric ammonium nitrate is (2 to 3): 1: (1 to 3), the concentration of the solution is 0.2 mol/L (relative to the diphenylphosphine oxide) by adding an organic solvent, then the mixed solution reacts for 6 hours at the reaction temperature of 40 DEG C, then thetemperature increases to 90 DEG C to react for 12 hours until the reaction is ended, the solvent is removed in a rotary evaporation manner, and the alkenyl diphenylphosphine compound is obtained by virtue of column chromatography. The method of the invention is simple in reaction system, easy in obtaining the initial raw materials, convenient in operation, and wider in substrate applicability.

Copper-catalyzed decarboxylative C-P cross-coupling of alkynyl acids with H-phosphine oxides: A facile and selective synthesis of (E)-1-alkenylphosphine oxides

A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.

Diphosphino-functionalized MCM-41-immobilized rhodium complex: A highly efficient and recyclable catalyst for the hydrophosphinylation of terminal alkynes

Diphosphino-functionalized MCM-41-immobilized rhodium complex (MCM-41-2P-RhCl3) was conveniently synthesized from commercially available and cheap γ-aminopropyltriethoxysilane via immobilization on mesoporous MCM-41, followed by reacting with diphenylphosphinomethanol and rhodium chloride. It was found that this heterogeneous rhodium complex is a highly efficient catalyst for the hydrophosphinylation of terminal alkynes with diphenylphosphine oxide and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity.

Copper-catalyzed C-P coupling through decarboxylation

An acid for a phosphine: A versatile protocol for preparation of various di(phenyl)phosphoryl oxides was developed by copper-catalyzed decarboxylative coupling of alkenyl, alkynyl carboxylic acids, and N-benzylproline, respectively, with R2P(O)