Complexes of functional phosphines. 4. Coordination properties of (diphenylphosphino)acetonitrile, ethyl (diphenylphosphino)acetate and corresponding carbanions. Characterization of a new facile reversible carbon dioxide insertion into palladium(II) complexes

Braunstein, Pierre; Matt, Dominique; Dusausoy, Y.; Fischer, Jean; Mitschler, A.; Ricard, Louis

doi:10.1021/ja00407a028

Cited by 147 publications

(84 citation statements)

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“…In the 31 P NMR spectrum, the phosphorus atom is observed at 25.7 ppm, a normal value for [PdCl(8-mq)(phosphine)] complexes. [17] In accord with the C 1 molecular symmetry, the Pd-bound CH 2 group of 10 appears as an ABX spectrum in the 1 H NMR spectrum, with δ A = 3.12 ppm and δ B = 2.42 ppm (J(BA) = 14.5 Hz; 3 J(PA) = 0 Hz and 3 J(PB) = 7.5 Hz). The PdCH B signal at 2.41 ppm is shifted somewhat upfield when compared with those of other [PdCl(8-mq)(phosphine)] complexes found in the literature (typical δ around 3.2 ppm).…”

Section: Catalytic Conversion Of Phosphine 3 To the Calix-fused Phospmentioning

confidence: 91%

“…The PdCH B signal at 2.41 ppm is shifted somewhat upfield when compared with those of other [PdCl(8-mq)(phosphine)] complexes found in the literature (typical δ around 3.2 ppm). [17] The observed shielding is likely to reflect the magnetic anisotropy created by the flat dibenzophospholyl unit located beneath one of the PdCH 2 atoms. This interpretation is consistent with the data inferred from the solid state structure of 10 (vide infra).…”

Section: Catalytic Conversion Of Phosphine 3 To the Calix-fused Phospmentioning

confidence: 99%

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Calix[4]arene-fused phospholes

et al. 2017

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A calix [4]arene-based biarylphosphine has been synthesised and catalytically converted into two diastereomeric, calixarene-fused phospholes. arene has been prepared and its coordinative properties investigated. When heated in the presence of palladium, the new biarylphosphine undergoes conversion into two diasteromeric, calixarene-fused phospholes. In both, the P lone pair adopts a fixed orientation with respect to the calixarene core. The more hindered phosphole (8), i.e. the one with the endo-oriented lone pair (cone angle 150°-175°), forms complexes having their metal centre positioned very near the calixarene unit but outside the cavity, this inducing an unusual chemical shift of one of the methylenic ArCH 2 Ar protons owing to interactions with the metal centre. As expected for dibenzophospholes, the complex [Rh(acac)(CO)•8], when combined with one equivalent of free 8, efficiently catalyses the hydroformylation of styrene, the catalytic system displaying high regioselectivity in favour of the branched aldehyde (b/l ratio up to 30). The optical and redox properties of the derivatives have also been investigated.

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Section: Catalytic Conversion Of Phosphine 3 To the Calix-fused Phospmentioning

confidence: 91%

Section: Catalytic Conversion Of Phosphine 3 To the Calix-fused Phospmentioning

confidence: 99%

Calix[4]arene-fused phospholes

et al. 2017

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“…The reaction diastereoselectively creates a new chiral centre at the deprotonated carbon atom, producing the single diastereoisomer, (S,R p )/(R,S p ), from the racemic ester. [58] Compared to the related complexes with chelating [R 2 PCHCO 2 Et] -anions, [59] compound 55 is chemically very robust, inert to air, CO, SO 2 , and some alkynes. (58), which was converted to acetate 59 and then to bromo alcohol 60 (Scheme 18).…”

Section: Rac-[2-(diphenylphosphanyl)ferrocenyl]acetic Acidmentioning

confidence: 99%

The Chemistry of Phosphanyl‐ferrocenecarboxylic Ligands

Štěpnička

2005

Eur J Inorg Chem

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The chemistry of ferrocene attracts considerable research interest even more than 50 years after its discovery, being stimulated mainly by applications of ferrocene ligands in catalysis. To the present day, the design of new ferrocene compounds ensued—sometimes by serendipity—the preparation of unprecedented coordination compounds and organometallic materials and, in the case of ferrocene compounds containing appropriate donor sets, led to numerous successful catalytic systems. This review provides a systematic survey of the chemistry of phosphanyl‐ferrocenecarboxylic ligands as a specific class of hybrid ferrocene ligands that emerged about ten years ago, illustrating their synthesis, coordination behaviour, and catalytic applications. Attention is also paid to the structural chemistry of these functional ferrocene ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…The discovery that certain nickel(I1) complexes incorporating mixed P,O donor ligands were effective catalyst precursors for ethylene oligomerization reactions in the so-called ShellHigher-Olefin-Process (SHOP) (1-7) has sparked a number of groups to devise new ancillary ligands that can be utilized (8)(9)(10)(11)(12)(13)(14). The original preparation (1) involved reaction of a ketophosphorus ylid of the type P h , P C H C O P h with Ni(COD), and PPh3 to produce, after phenyl transfer, the complex Ni(Ph)PPh,[Ph,PCH=C(O)Ph].…”

Section: Introductionmentioning

confidence: 99%

Coordination chemistry of a mixed donor bidentate ligand with nickel. A tetrameric enolate of sodium that binds a phosphine donor

Fryzuk¹,

Gao²,

Rettig³

1995

Can. J. Chem.

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The preparation of a mixed donor ligand consisting of an enolate and neutral phosphine is described and its coordination chemistry with nickel reported. The phosphino ketones R,PCH,COPh (R = Cy or Pri) are prepared by the reaction of the corresponding secondary phosphines with bromoacetophenone to form the corresponding phosphonium salts [R,P(H)CH,COPh]+Br-(R = Cy or Pi); subsequent deprotonation leads to the neutral ketones. The enolates are formed by addition of NaN(SiMe,), to the neutral ketone. The crystal structure of the sodium enolate having isopropyl substituents at phospho~us displays a tetrameric structure in the solid state and there is an interaction of the phosphorus donor with the sodium anion: Na-P, 2.852(2) A. The preparation of a series of nickel complexes was achieved by addition of the sodium enolate to the appropriate Ni(I1) starting material. The structures of the nickel derivatives are reported. The catalytic behaviour of one of these complexes in the polymerization and oligomerization of ethylene is briefly described. ' Author to whom correspondence may be addressed. Telephone: (604)

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Complexes of functional phosphines. 4. Coordination properties of (diphenylphosphino)acetonitrile, ethyl (diphenylphosphino)acetate and corresponding carbanions. Characterization of a new facile reversible carbon dioxide insertion into palladium(II) complexes

Abstract: The coordination properties of Ph2PCH2CN (L1) and Ph2PCH2COOC2H5 (L2) have been investigated. Complexes

Cited by 147 publications

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Calix[4]arene-fused phospholes

Calix[4]arene-fused phospholes

The Chemistry of Phosphanyl‐ferrocenecarboxylic Ligands

Coordination chemistry of a mixed donor bidentate ligand with nickel. A tetrameric enolate of sodium that binds a phosphine donor

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