1159205-36-3

Upstream product

• 3156-37-4 (E)-1-bromo-4-(2-nitrovinyl)benzene 
• 122-52-1 triethyl phosphite 
• 75-52-5 nitromethane 
• 1122-91-4 4-bromo-benzaldehyde 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 762-04-9 phosphonic acid diethyl ester 
• 69151-18-4 1-bromo-4-(1-bromovinyl)benzene 
• 38318-52-4 α-bromovinylphosphonic acid diethyl ester 
• 374564-35-9 potassium 4-bromophenyltrifluoroborate 
• 5467-74-3 4-Bromophenylboronic acid 
• 243137-79-3 1,1,2,2,3,3,4,4,4-nonafluoro-butane-1-sulfonic acid 1-(diethoxy-phosphoryl)-vinyl ester 
• 37016-53-8 1-(4-bromophenyl)vinylphosphonic acid 
• 122-51-0 orthoformic acid triethyl ester 

Relevant academic research and scientific papers

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.

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.

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.

Pd-Catalyzed Synthesis of α-Aryl Vinylphosphonates via Suzuki Arylation of α-Phosphonovinyl Nonaflates

The first palladium-catalyzed method for the arylation of α-phosphonovinyl nonaflates is described. Using a catalyst comprised of Pd(OAc)2 and SPhos, terminal and internal α-aryl vinylphosphonates could be efficiently accessed under mild condit

A simple and efficient method for one-pot, three-component synthesis of terminal vinylphosphonates using a task-specific ionic liquid

A convenient and practical method for the one-pot, three-component synthesis of terminal vinylphosphonates from readily available starting materials (aryl/alkyl/heteroaryl aldehydes, nitromethane and trialkylphosphites) through a tandem Henry-Michael reaction followed by nitro elimination in the presence of 5-hydroxypentylammonium acetate (5-HPAA) as a task-specific ionic liquid, is described. This method offers several advantages such as the use of a reusable and inexpensive ionic liquid, which is an environmentally benign reaction medium, and a simple reaction setup that does not require specialized equipment. The approach offers good yields of the products under mild reaction conditions. Georg Thieme Verlag Stuttgart New York.

Synthesis of vinylphosphonates and its first exploration of bioactivity

Phosphonation of β-nitro-alkene with triethyl phosphite was achieved under microwave irradiation using CH2Cl2 as the solvent in the absence of catalyst with moderate to high yields (up to 90%). This method of formation of carbonphosphor bonds is simple, mild, convenient and effective. Synchronously, a number of vinylphosphonates derivatives were synthesized and evaluated biologically preliminary.

Enantioselective synthesis of chiral α-aryl or α-alkyl substituted ethylphosphonates via Rh-catalyzed asymmetric hydrogenation with a P-stereogenic BoPhoz-type ligand

(Chemical Equation Presented) An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding α,β- unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.