25944-64-3

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 85166-79-6 Methanesulfonic acid 1-(diethoxy-phosphoryl)-1-phenyl-ethyl ester 
• 64-19-7 acetic acid 
• 16212-06-9 phenyl styryl sulfone 
• 762-04-9 phosphonic acid diethyl ester 
• 98-81-7 1-bromovinylbenzene 
• 536-74-3 phenylacetylene 
• 3220-50-6 1-phenylvinylphosphonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 2303-76-6 sodium diethyl phosphite 
• 219501-21-0 Se-(β-oxo-β-phenylethyl) O,O-diethylselenophosphate 
• 50-00-0 formaldehyd 

Downstream Products

• 82632-34-6 2-phenyl-3H-pyrrolizine 
• 33973-48-7 diethyl (1-phenylethyl)phosphonate 
• 444789-01-9 (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 
• 444789-04-2 (2S,5R,2'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 
• 261167-64-0 (2S,5R,2'R)-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-methylpyrazine 
• 261167-65-1 (2S,5R,2'S)-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-methylpyrazine 
• 261167-71-9 (1S,3S)-(3-amino-4-hydroxy-3-methyl-1-phenylbutyl)phosphonic acid 
• 1133079-40-9 diethyl (3-phenyl-4,5-dihydro-3H-pyrazol-3-yl)phosphonate 
• 13599-12-7 ethyl 3-phenyl-1H-pyrazole-5-carboxylate 
• 7749-92-0 diethyl 2-formyl-1-phenylethylphosphonate 
• 884489-14-9 (3-benzyloxyamino-1-phenyl-propyl)-phosphonic acid diethyl ester 
• 852326-96-6 [3-(acetyl-benzyloxy-amino)-1-phenyl-propyl]-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Highly enantioselective hydrogenation of α,β-unsaturated phosphonates with iridium-phosphinooxazoline complex: Synthesis of a phosphorus analogue of naproxen

A number of pharmaceutically interesting optically active 1-arylethylphosphonates, including a phosphorus analogue of naproxen, has been synthesized with ee 92-95% via asymmetric hydrogenation under mild conditions using [Ir(cod)(phosphine oxazoline)]sup

Synthesis of Terminal Vinylphosphonates Via Dbu-Promoted Tandem Phospha-Michael/Elimination Reactions

The terminal vinylphosphonates were prepared from various β-nitroolefins and phosphites through tandem phospha-Michael/elimination reactions. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a variety of new vinylphosphonates were obtained in

Asymmetric hydrogenation of diethyl 1-phenylvinylphosphonate by metal complexes in CH2Cl2 and in supercritical carbon dioxide using phosphite-type ligands

Asymmetric hydrogenation of diethyl 1-phenylvinylphosphonate was carried out for the first time in dichloromethane and supercritical carbon dioxide in the presence of phosphite and amidophosphite ligands. The catalysts based on [Ir(COD)2]BARF (COD is 1,5-

Lewis Acid Enables Ketone Phosphorylation: Synthesis of Alkenyl Phosphonates

An efficient Lewis acid enabled ketones phosphonylation to synthesize vinylphosphonates has been developed. This method relays on ketone hydrophosphonylation/α-hydroxy phosphonates unimolecular elimination (E1) dehydration cascade reaction sequence. Vario

Markovnikov-addition of H-phosphonates to terminal alkynes under metal- And solvent-free conditions

An addition of H-phosphonates to aryl alkynes was realized under solvent- and metal-free conditions, affording Markovnikov-selective α-vinylphosphonates in moderate to good yields. A wide range of aryl alkynes could be applied for the reaction. A tentative mechanism of addition-substitution was proposed based onin situ31P {1H} NMR studies.

Transition metal-free and regioselective vinylation of phosphine oxides and: H -phosphinates with VBX reagents

A series of phosphine oxides and H-phosphinates were vinylated in the presence of the iodine(iii) reagents vinylbenziodoxolones (VBX), providing the corresponding alk-1-enyl phosphine oxides and alk-1-enyl phosphinates in good yields with complete chemo- and regioselectivity. The vinylation proceeds in open flask under mild and transition metal-free conditions.

Rhenium-Catalyzed Decarboxylative Tri-/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid-Derived Hypervalent Iodine Reagents

Herein, unprecedented rhenium-catalyzed decarboxylative oxytri-/difluoromethylation and Heck-type trifluoromethylation of styrenes have been developed by using hypervalent iodine(III) reagents derived from cheap, stable, and easy-handling fluorinated carboxylic acids. Mechanistic studies revealed a radical decarboxylative trifluoromethylation pathway occurring in these reactions.

Hydrophosphorylation of Alkynes Catalyzed by Palladium: Generality and Mechanism

We carried out a comprehensive study on the generality, scope, limitations, and mechanism of the palladium-catalyzed hydrophosphorylation of alkynes with P(O)-H compounds (i.e., H-phosphonates, H-phosphinates, secondary phosphine oxides, and hypophosphinic acid). For H-phosphonates, Pd/dppp was the best catalyst. Both aromatic and aliphatic alkynes, with a variety of functional groups, were applicable to produce the Markovnikov adducts in high yields with high regioselectivity. Aromatic alkynes showed higher reactivity than aliphatic alkynes. Terminal alkynes reacted faster than internal alkynes. Sterically crowded H-phosphonates disfavored the addition. For H-phosphinates and secondary phosphine oxides, Pd/dppe/Ph2P(O)OH was the catalyst of choice, which led to highly regioselective formation of the Markovnikov adducts. By using Pd(PPh3)4 as the catalyst, hypophosphinic acid added to terminal alkynes to give the corresponding Markovnikov adducts. Phosphinic acids, phosphonic acid, and its monoester were not applicable to this palladium-catalyzed hydrophosphorylation. Mechanistic studies showed that, with a terminal alkyne, (RO)2P(O)H reacted, like a Br?nsted acid, to selectively generate the α-alkenylpalladium intermediate via hydropalladation. On the other hand, Ph(RO)P(O)H and Ph2P(O)H gave a mixture of α- and β-alkenylpalladium complexes. In the presence of Ph2P(O)OH, hydropalladation with this acid took place first to selectively generate the α-alkenylpalladium intermediate. A subsequent ligand exchange with a P(O)H compound gave the phosphorylpalladium intermediate which produced the Markovnikov adduct via reductive elimination. Related intermediates in the catalytic cycle were isolated and characterized.

Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: A general protocol for the synthesis of terminal α-substituted vinylphosphonates

A general and robust protocol for the synthesis of terminal α-substituted vinylphosphonates via Suzuki coupling of α-bromovinylphosphonates with organotrifluoroborates has been successfully developed. This method features a broad substrate scope, great functional group compatibilities, and easy scale-up ability. In addition to easy access of nucleophiles, a straightforward synthesis of electrophiles was also realized with diethyl α-bromoethenylphosphonate as the starting material. With a combination of Pd2(dba)3/SPhos as the catalyst, a range of α-alkyl, aryl, heteroaryl, and alkynyl substituted ethenylphosphonates could be nicely accessed under mild conditions. As a synthetic application, the terminal vinylphosphonate was utilized as an effective Michael acceptor in the visible-light-promoted Giese reaction.

Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis

A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g