Facile synthesis of aryl(difluoromethyl)phosphonates through CuBr-mediated cross coupling reactions of [(diethoxyphosphinyl)difluoromethyl]zinc bromide with aryl iodides

Yokomatsu, Tsutomu; Murano, Tetsuo; Suemune, Kenji; Shibuya, Shiroshi

doi:10.1016/s0040-4020(96)01063-0

Cited by 86 publications

(39 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Generally, electron‐rich aryl boronic acids 5 provided the corresponding difluoromethylated phosphonates in high yields ( 3 b – e , 3 g – i ). This is in sharp contrast to previous results, in which the reactions of aromatic derivatives that bear an electron‐donating group proceeded with low reaction efficiency 8e. 10c Electron‐deficient substrates 5 were also smoothly transformed when 3 Å molecular sieves (MS) were employed as an additive ( 3 j – l ).…”

Section: Methodscontrasting

confidence: 91%

Palladium‐Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives

et al. 2014

View full text Add to dashboard Cite

The palladium-catalyzed difluoroalkylation of aryl boronic acids with bromodifluoromethylphosphonate, bromodifluoroacetate, and further derivatives has been developed. This method provides a facile and useful access to a series of functionalized difluoromethylated arenes (ArCF 2 PO(OEt) 2 , ArCF 2 CO 2 Et, and ArCF 2 CONR 1 R 2 ) that have important applications in drug discovery and development. Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway may be involved in the catalytic cycle.

show abstract

Section: Methodscontrasting

confidence: 91%

Palladium‐Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives

et al. 2014

View full text Add to dashboard Cite

show abstract

“…The required F2pmp building block was directly synthesized by copper mediated cross coupling of an organozinc compound in analogy to published procedures [26-31]. …”

Section: Resultsmentioning

confidence: 99%

Probing SH2-domains using Inhibitor Affinity Purification (IAP)

et al. 2014

View full text Add to dashboard Cite

BackgroundMany human diseases are correlated with the dysregulation of signal transduction processes. One of the most important protein interaction domains in the context of signal transduction is the Src homology 2 (SH2) domain that binds phosphotyrosine residues. Hence, appropriate methods for the investigation of SH2 proteins are indispensable in diagnostics and medicinal chemistry. Therefore, an affinity resin for the enrichment of all SH2 proteins in one experiment would be desirable. However, current methods are unable to address all SH2 proteins simultaneously with a single compound or a small array of compounds.ResultsIn order to overcome these limitations for the investigation of this particular protein family in future experiments, a dipeptide-derived probe has been designed, synthesized and evaluated. This probe successfully enriched 22 SH2 proteins from mixed cell lysates which contained 50 SH2 proteins. Further characterization of the SH2 binding properties of the probe using depletion and competition experiments indicated its ability to enrich complexes consisting of SH2 domain bearing regulatory PI3K subunits and catalytic phosphoinositide 3-kinase (PI3K) subunits that have no SH2 domain.ConclusionThe results make this probe a promising starting point for the development of a mixed affinity resin with complete SH2 protein coverage. Moreover, the additional findings render it a valuable tool for the evaluation of PI3K complex interrupting inhibitors.

show abstract

“…The starting diethyl phosphonates 6a-e were prepared according to the method described previously, and transformed into the corresponding free acids 1a-e by TMSBr-mediated deprotection. 8,9,12 Treatment of 1a-e with oxalyl chloride in boiling CH 2 Cl 2 in the presence of N,Ndimethylaminopyridine (DMAP) and DMF for 10 h gave the corresponding dichlorides, which were subsequently treated with 2-cyanoethanol in pyridine to give the bis-(2-cyanoethyl) esters 7a-e in 72-91% yield. Thionylation of 7a-e with Lawesson's reagent [2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] in toluene at 100 °C gave 8a-e in 47-91% yield.…”

Section: Methodsmentioning

confidence: 99%

The difluoromethylenephosphonothioic acid group as a phosphate surrogate for obtaining PTP-1B inhibitors. Transformation of difluoromethylenephosphonic acids into difluoromethylenephosphonothioic acids

Murano¹,

Takechi²,

Yuasa³

et al. 2003

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

Facile synthesis of aryl(difluoromethyl)phosphonates through CuBr-mediated cross coupling reactions of [(diethoxyphosphinyl)difluoromethyl]zinc bromide with aryl iodides

Cited by 86 publications

References 23 publications

Palladium‐Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives

Palladium‐Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives

Probing SH2-domains using Inhibitor Affinity Purification (IAP)

The difluoromethylenephosphonothioic acid group as a phosphate surrogate for obtaining PTP-1B inhibitors. Transformation of difluoromethylenephosphonic acids into difluoromethylenephosphonothioic acids

Contact Info

Product

Resources

About