1159205-35-2

Upstream product

• 1159205-39-6 1-(4-fluorophenyl)vinylphosphonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 38318-52-4 α-bromovinylphosphonic acid diethyl ester 
• 1765-93-1 4-fluoroboronic acid 
• 243137-79-3 1,1,2,2,3,3,4,4,4-nonafluoro-butane-1-sulfonic acid 1-(diethoxy-phosphoryl)-vinyl ester 
• 919-19-7 diethyl acetylphosphonate 
• 1309980-37-7 diethyl 1-[(4-methylbenzenesulfonyl)oxy]ethene-alpha-phosphonate 

Downstream Products

• 1159205-41-0 rac-[1-(4-fluoro-phenyl)-ethyl]-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

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

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.

α-Phosphonovinyl Arylsulfonates: An Attractive Partner for the Synthesis of α-Substituted Vinylphosphonates through Palladium-Catalyzed Suzuki Reactions

It has been demonstrated that a variety of α-phosphonovinyl arylsulfonates with electron-neutral, -donating, and -withdrawing groups on the phenyl ring could be conveniently and efficiently prepared. In the presence of a Pd(OAc)2/SPhos-based catalyst, various organoboron compounds could be employed as the nucleophilic coupling partners, such as organoboronic acids, boronate esters, and organotrifluoroborates. The newly developed O-centered electrophiles could couple with a multitude of aryl, heteroaryl, and alkylboron reagents, to give α-substituted vinylphosphonates in moderate to excellent yields. Generally, the Suzuki reaction is tolerant of extensive substitution at the aromatic ring of both electrophilic and nucleophilic coupling partners. As in the case of the Suzuki reaction of 8-quinolineboronic acid, proper choice of α-phosphonovinyl arylsulfonates is critical to efficient coupling. Moreover, the prospect for application of this method to complex synthesis has been demonstrated through the coupling of estrone-derived arylborons. The present protocol also features mild conditions and high efficiency. A new and attractive coupling partner for the synthesis of α-substituted vinylphosphonates through Suzuki reactions has been developed. The developed O-centered electrophiles couple with various organoboron reagents to give α-substituted vinylphosphonates in moderate to excellent yields. This protocol features broad substrate scope, mild conditions, and high efficiency.

Applications of α-phosphonovinyl tosylates in the synthesis of α-arylethenylphosphonates via suzuki-miyaura cross-coupling reactions

It has been demonstrated for the first time that α-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access α-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.

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.