42009-12-1

Upstream product

• 98-88-4 benzoyl chloride 
• 1733-57-9 ethydiphenylphosphine oxide 
• 93-89-0 benzoic acid ethyl ester 
• 1733-58-0 phenacyldiphenylphosphine oxide 
• 74-88-4 methyl iodide 
• 99639-13-1 C₂₇H₂₅N₂P 
• 100-52-7 benzaldehyde 
• 2157-50-8 propiophenone oxime 
• 93-55-0 1-phenyl-propan-1-one 
• 108-86-1 bromobenzene 
• 673-32-5 1-Phenylprop-1-yne 
• 4559-70-0 Diphenylphosphine oxide 
• 2890-85-9 N-acetyl-1-phenylpropenamine 
• 637-50-3 1-phenylpropene 

Downstream Products

• 63103-81-1 (1RS,2RS)-1-phenyl-2-(diphenylphosphinoyl)propan-1-ol 
• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 63103-81-1 (1RS,2SR)-1-phenyl-2-(diphenylphosphinoyl)propan-1-ol 
• 63103-81-1 2-(Diphenyl-phosphinoyl)-1-phenyl-propan-1-ol 
• 63103-81-1 2-(Diphenyl-phosphinoyl)-1-phenyl-propan-1-ol 
• 784082-51-5 (1-hydroxy-1-phenylpropan-2-yl)diphenylphosphine oxide 

Relevant academic research and scientific papers

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

Visible light-promoted metal-free aerobic oxyphosphorylation of olefins: A facile approach to β-ketophosphine oxides

A metal-free direct aerobic oxyphosphorylation of alkenes with H-phosphine oxides has been developed utilizing visible light photoredox catalysis. A variety of β-ketophosphine oxides have been obtained in good yields from simple olefins under air with ine

Copper-Catalyzed Direct Oxyphosphorylation of Enamides with P(O)-H Compounds and Dioxygen

A simple and convenient copper-catalyzed direct oxyphosphorylation of enamides with P(O)-H compounds and dioxygen has been developed under mild conditions. This methodology can allow the synthesis of a series of valuable β-ketophosphine oxides/β-ketophosphonates in moderate to good yields with a broad substrate scope simply by using readily-available starting materials.

Copper catalyzed one-pot synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides

A facile and efficient copper catalyzed one-pot method has been developed for the formation of β-ketophosphine oxides from ketones and H-phosphine oxides under air at room temperature, in which vinylhydrazinedicarboxylate was formed as the key intermediate. Preliminary mechanistic studies indicated that the reaction might involve a radical process and carbonyl oxygen atom of β-ketophosphine oxides came from molecular oxygen.

Copper-catalyzed direct oxyphosphorylation of alkynes with H-phosphine oxides and dioxygen: A convenient approach to β-ketophosphine oxides

A simple and facile copper-catalyzed synthesis of β-ketophosphine oxides via direct oxyphosphorylation of alkynes with H-phosphine oxides and dioxygen has been developed under mild conditions without any base or cocatalyst. A radical reaction pathway for

Copper-Catalyzed radical/radical Csp3-H/P-H cross-Coupling: α-Phosphorylation of aryl ketone O-Acetyloximes

The selective radical/radical cross-coupling of two different organic radicals is a great challenge due to the inherent activity of radicals. In this paper, a copper-catalyzed radical/radical Csp3-H/P-H cross-coupling has been developed. It provides a radical/radical cross-coupling in a selective manner. This work offers a simple way toward β-ketophosphonates by oxidative coupling of aryl ketone o-acetyloximes with phosphine oxides using CuCl as catalyst and PCy3 as ligand in dioxane under N2 atmosphere at 130 C for 5 h, and yields ranging from 47% to 86%. The preliminary mechanistic studies by electron paramagnetic resonance (EPR) showed that, 1) the reduction of ketone o-acetyloximes generates iminium radicals, which could isomerize to α-sp3-carbon radical species; 2)phosphorus radicals were generated from the oxidation of phosphine oxides. Various aryl ketone o-acetyloximes and phosphine oxides were suitable for this transformation.

The synthesis of alkenes via epi-phosphonium species: 1. An anti-Wittig elimination

Anti-1,2-phosphinyl alcohols 11 and their corresponding syn-isomers upon treatment with phosphorus trichloride and triethylamine give E and Z alkenes respectively, by an anti elimination. This is in marked contrast to the syn Horner-Wittig elimination of the corresponding 1,2-phosphinoyl alcohols. The 1,2-phosphinyl alcohols 11 were prepared by the reduction of 1,2-phosphinoyl alcohols with cerium(III) chloride/lithium aluminium hydride. The anti elimination is explained by the formation of a transient epi-phosphonium species. An unexpected E-selective Horner-Wittig elimination during the cerium(III) chloride/lithium aluminium hydride reduction of a 1,2-phosphinoyl alcohol in which the diphenylphosphinoyl group is adjacent to an aryl group is described. This led to the synthesis of the antimitotic agent E- combretastatin A-4. An alternative synthesis of the 1,2-phosphinyl alcohols from the corresponding phosphine-borane complex is also described.

Opposite stereochemical effects exerted by CeCl3 and TiCl4 on the Lewis acid mediated reduction of α-alkyl-β-ketophosphine oxides with metallic hydrides: A highly stereoselective protocol for the synthesis of syn and anti α-alkyl-β-hydroxyphosphine oxides

A general, highly efficient methodology for obtaining both syn and anti α-hydroxyphosphine oxides by reduction of the corresponding α-ketophosphine oxides is described. The nature of the Lewis acid was found to be pivotal in determining the outcome of these reactions. Strongly chelating TiCl4 led to the anti isomer in high diastereoisomeric excess in noncoordinating solvents (CH2Cl2) at -78°C with BH3/py as reducing agent, while nonchelating CeCl3 gave a high excess of the syn isomer in coordinating solvents (THF) at the same temperature with LiBH4 as reducing agent. In the latter case, CeCl3 is essential in achieving high yields and stereoselectivity, since it allows the reaction to be performed at low temperatures. Otherwise, higher temperatures (0 °C) are required, which lower both yields and selectivities. Moreover, each step of the protocol for the synthesis of stereodefined disubstituted olefins from alkylphosphine oxides (Warren's modification of the Homer procedure) has been optimized, and the optimized procedure has been applied to the synthesis of muscalure, the pheromone of the domestic fly.

TiCl4 mediated LiBH4 reduction of β-ketophosphine oxides: A high stereoselective route to the synthesis of anti-β-hydroxyphosphine oxides

The reduction of an α-alkyl-β-ketophosphine oxide with LiBH4 in presence of a strong chelating agent, such as TiCl4, gives the corresponding β-hydroxyphosphine oxide in high yields and with high anti-diastereoselectivity independently from the size of both the α- and β-alkyl chains.