79349-13-6

Usage

Uses

Used in Organometallic Chemistry:
Benzonitrile, 4-[2-(diphenylphosphinyl)ethenyl]-, (E)is used as a phosphine ligand for the formation of stable and reactive complexes with metal ions in organometallic chemistry. Its coordination with metal ions such as palladium, platinum, and copper enhances the reactivity and stability of the resulting complexes.
Used in Catalysis:
In the field of catalysis, Benzonitrile, 4-[2-(diphenylphosphinyl)ethenyl]-, (E)is used as a ligand in the development of catalysts for various chemical reactions. The complexes formed with metal ions have been employed in cross-coupling reactions, hydrogenation, and C-H activation, making Benzonitrile, 4-[2-(diphenylphosphinyl)ethenyl]-, (E)- a valuable asset in the advancement of catalytic processes.
Used in Pharmaceutical Industry:
Benzonitrile, 4-[2-(diphenylphosphinyl)ethenyl]-, (E)is used as a building block and intermediate in the synthesis of pharmaceutical compounds. Its unique coordination properties and reactivity make it a promising candidate for the development of new drugs and drug delivery systems.
Used in Material Science:
In material science, Benzonitrile, 4-[2-(diphenylphosphinyl)ethenyl]-, (E)is utilized in the synthesis of advanced materials, such as organic semiconductors and catalysts for polymerization reactions. Its ability to form stable complexes with metal ions contributes to the development of new materials with improved properties and applications.

Upstream product

• 23176-18-3 bis(diphenylphosphino)methane monooxide 
• 4559-70-0 Diphenylphosphine oxide 
• 16642-94-7 (E)-4-cyanocinnamic acid 
• 3032-92-6 4-cyanophenylacetylene 
• 3435-51-6 4-ethenylbenzonitrile 
• 4712-55-4 diphenyl hydrogen phosphite 
• 18664-39-6 3-(4-cyanophenyl)acrylic acid 
• 94394-65-7 4-((E)-2-Diphenylphosphanyl-vinyl)-benzonitrile 

Downstream Products

• 82943-04-2 (E)-4-(2-(diphenylphosphorothioyl)vinyl)benzonitrile 

Relevant academic research and scientific papers

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.

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

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.

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)

Preparation of β-Substituted trans-Ethylene Diphenylphosphines and Sulphides by P(O) and P(S)-activated Olefination

Methylene bis-diphenylphosphine monoxide (3c) in toluene reacts regiospecifically and stereoselectively with aldehydes in the presence of potassium tert-butoxide to β-substituted trans-ethylene diphenylphosphines 6, which can be oxidized to the sulphides 2 by sulphur in acetone.These sulphides 2 are to be obtained also directly from methylene bis-diphenylphosphine oxide sulphide 3b and methylene bis-diphenylphosphine disulphide 3d, respectively, under the same olefination conditions.But the yields are smaller and the purification of the raw products is much more difficult, if 3d is used.