2017
DOI: 10.1021/acsomega.7b01424
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Sequential Electrophilic Substitution Reactions of Tungsten-Coordinated Phosphenium Ions and Phosphine Triflates

Abstract: 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 … Show more

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Cited by 16 publications
(14 citation statements)
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“…Similar C-H activation of arenes by phosphorus-containing electrophiles has been described for metal-stabilized phosphenium triates. [42][43][44] Despite its instability in solution, 3[OTf] can be stored in the solid state at À35 C for weeks without decomposition and puried by recrystallization from saturated dichloromethane/ pentane solutions, also at À35 C. Treatment of 3[OTf] with a chloride source (tetra-n-butylammonium chloride) in chloroform at 23 C quantitatively generated 1, [TBA][OTf] and anthracene (Scheme 1). This reactivity is consistent with nucleophilic attack of the phosphonium center in 3[OTf] by chloride, inducing reductive loss of anthracene.…”
mentioning
confidence: 99%
“…Similar C-H activation of arenes by phosphorus-containing electrophiles has been described for metal-stabilized phosphenium triates. [42][43][44] Despite its instability in solution, 3[OTf] can be stored in the solid state at À35 C for weeks without decomposition and puried by recrystallization from saturated dichloromethane/ pentane solutions, also at À35 C. Treatment of 3[OTf] with a chloride source (tetra-n-butylammonium chloride) in chloroform at 23 C quantitatively generated 1, [TBA][OTf] and anthracene (Scheme 1). This reactivity is consistent with nucleophilic attack of the phosphonium center in 3[OTf] by chloride, inducing reductive loss of anthracene.…”
mentioning
confidence: 99%
“…Using this method, chiral phosphine ligands containing primary alkyl, sec-alkyl or aromatic substituents, including ferrocenyl and phenyl groups, were obtained. Phosphine ligands were used in the asymmetric catalytic reduction of alkynes and aldehydes with formation of chiral allyl alcohols with high regioselectivity and full (E)-selectivity as shown in Equation (33) [48]. Reactions of P-chiral secondary phosphine-boranes with fluorobenzene tricarbonylchromium in the presence of sec-butyl lithium led to the formation of phosphine ligands in yields of 75-99% and complete retention of the absolute configuration (Equation (32)) [47].…”
Section: (28)mentioning
confidence: 99%
“…Using this method, chiral phosphine ligands containing primary alkyl, sec-alkyl or aromatic substituents, including ferrocenyl and phenyl groups, were obtained. Phosphine ligands were used in the asymmetric catalytic reduction of alkynes and aldehydes with formation of chiral allyl alcohols with high regioselectivity and full (E)-selectivity as shown in Equation (33) [48].…”
Section: (28)mentioning
confidence: 99%
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