23901-75-9

Upstream product

• 1101-41-3 Tetraphenyldiphosphin 
• 766-97-2 4-n-methylphenylacetylene 
• 4559-70-0 Diphenylphosphine oxide 
• 23176-18-3 bis(diphenylphosphino)methane monooxide 
• 1866-39-3 4-methylcinnamic acid 
• 829-85-6 diphenylphosphane 
• 100-58-3 phenylmagnesium bromide 
• 1831-63-6 diphenylphosphorylacetic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 1866-39-3 trans-p-methylcinnamic acid 
• 4712-55-4 diphenyl hydrogen phosphite 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 60512-56-3 1-(2,2-dibromovinyl)-4-methylbenzene 

Downstream Products

• 82943-02-0 (E)-(4-methylstyryl)diphenylphosphine sulfide 

Relevant academic research and scientific papers

Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes

An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. The success of the reaction was fo

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.

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).

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

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.

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.

Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides

A radical-mediated approach has been introduced for the C-S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.

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.

Experimental and theoretical studies on nickel-zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)-H compounds

A new stereoselective one-pot protocol for the preparation of E-alkenyl-phosphorus compounds under catalysis of an inexpensive nickel-zinc catalyst system has been developed, which provides a potential useful method for C-P bond formation. 31P NMR spectrum and density functional theory calculations were performed to study the reaction mechanism.