Sequential electrophilic P–C bond formation in metal-coordinated chlorophosphines

Jayaraman, Arumugam; Jacob, Tyler V.; Bisskey, Jeff; Sterenberg, Brian T.

doi:10.1039/c5dt01281c

Cited by 11 publications

(30 citation statements)

References 30 publications

(12 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We used metal-mediated electrophilic substitution 20 21 22 to rapidly generate a diverse initial library of synthetic organophosphorus compounds containing carbon-phosphorus bonds. One compound in the library, 9aWC2, a tungsten phosphine complex ( Fig.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

A potent synthetic inorganic antibiotic with activity against drug-resistant pathogens

Hubick

Jayaraman

McKeen

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

The acronymously named “ESKAPE” pathogens represent a group of bacteria that continue to pose a serious threat to human health, not only due to their propensity for repeated emergence, but also due to their ability to “eskape” antibiotic treatment12. The evolution of multi-drug resistance in these pathogens alone has greatly outpaced the development of new therapeutics, necessitating an alternative strategy for antibiotic development that considers the evolutionary mechanisms driving antibiotic resistance. In this study, we synthesize a novel inorganic antibiotic, phosphopyricin, which has antibiotic activity against the Gram-positive methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE). We show that this potent antibiotic is bactericidal, and exhibits low toxicity in an acute dose assay in mice. As a synthetic compound that does not occur naturally, phosphopyricin would be evolutionarily foreign to microbes, thereby slowing the evolution of resistance. In addition, it loses antibiotic activity upon exposure to light, meaning that the active antibiotic will not accumulate in the general environment where strong selective pressures imposed by antibiotic residuals are known to accelerate resistance. Phosphopyricin represents an innovation in antimicrobials, having a synthetic core, and a photosensitive chemical architecture that would reduce accumulation in the environment.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Compounds 9aWC2, 9bWC2, 9bWC3, 10bW, and 11bW were synthesized using published procedures 20 21 22 . 9bWC2 and 9bWC3 are isomers that result from C2 or C3 substitution of the phosphine on the pyrrole ring, and were separated for the bioassays as described previously 12 .…”

Section: Methodsmentioning

confidence: 99%

A potent synthetic inorganic antibiotic with activity against drug-resistant pathogens

Hubick

Jayaraman

McKeen

et al. 2017

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

“…The phosphine triflate 3 reacts with a wide range of organic nucleophiles, allowing for the controlled introduction of single substituents onto phosphorus. For example, the activated aromatic compounds N , N -diethylaniline and anisole readily add to 3 , leading to the expected para-substituted products 4 (16) and 5 (Scheme 5). Both of these reactions are rapid at RT and high-yielding.…”

Section: Resultsmentioning

confidence: 99%

“…This is illustrated here by the addition of allylTMS and then AlCl 3 to compound 4 , which leads to the allyl-anilinyl-phenyl phosphine complex 23 (Scheme 10). 16…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Sequential Electrophilic Substitution Reactions of Tungsten-Coordinated Phosphenium Ions and Phosphine Triflates

et al. 2017

Self Cite

View full text Add to dashboard Cite

ion of chloride from [W(CO) 5 {PPhCl 2 }] with AgOSO 2 CF 3 leads to the phosphine triflate complex [W(CO) 5 {PPhCl(OSO 2 CF 3 )}] which undergoes electrophilic substitution reactions with N , N -diethylaniline, anisole, N , N -dimethyl- p -toluidine, toluene, biphenyl, naphthalene, 2,7,9,9-tetramethyl xanthene, and allyltrimethylsilane to form the chlorophosphine complexes [W(CO) 5 {PPhClR}], where R = p -diethylanilinyl, p -anisyl, 2-( N , N -dimethyl-4-methylphenyl), p -tolyl, p -phenylphenyl, 1-naphthyl, 4-(2,7,9,9-tetramethylxanthyl), and allyl. Abstraction of the second chloride with AgOSO 2 CF 3 leads, in most cases, to the respective phosphine triflates [W(CO) 5 {PPhR(OSO 2 CF 3 )}], which react with ferrocene to form the ferrocenyl phosphine complexes [W(CO) 5 {PPhR(C 10 H 9 Fe)}]. The W(CO) 5 unit can be removed via photolysis in the presence of bis(diphenylphosphino)ethane to form metal-free phosphines.

show abstract

Group VI Metal Complexes of Carbon Monoxide and Isocyanides

Fischer

2022

Comprehensive Organometallic Chemistry IV

View full text Add to dashboard Cite

Sequential electrophilic P–C bond formation in metal-coordinated chlorophosphines

Cited by 11 publications

References 30 publications

A potent synthetic inorganic antibiotic with activity against drug-resistant pathogens

A potent synthetic inorganic antibiotic with activity against drug-resistant pathogens

Sequential Electrophilic Substitution Reactions of Tungsten-Coordinated Phosphenium Ions and Phosphine Triflates

Group VI Metal Complexes of Carbon Monoxide and Isocyanides

Contact Info

Product

Resources

About