New Trends in Hexacoordinated Phosphorus Chemistry

Constant, Samuel; Lacour, Jérôme

doi:10.1007/b100980

Cited by 24 publications

(3 citation statements)

References 24 publications

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“…Many derivatives of varied charge and geometry have been synthesized in studies devoted to phosphorus reactivity. A large number of compounds have also been prepared for applications in fields as varied as classical organic chemistry, stereoselective synthesis and analysis [8,9], bioorganic chemistry, electrochemistry and photochemistry [10]. This personal account will, however, concentrate its attention on a single aspect of this chemistry, that of the anionic hexacoordinated phosphates -and on their use as chiral NMR solvating, resolving and asymmetry-inducing reagents, in particular.…”

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confidence: 99%

Chiral hexacoordinated phosphates: From pioneering studies to modern uses in stereochemistry

Lacour

2010

Comptes Rendus. Chimie

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Chiral cationic molecular structures and supramolecular assemblies can be effectively analyzed, resolved and stereocontrolled through an asymmetric ion pairing with enantiopure hexacoordinated phosphate anions like TRISPHAT or BINPHAT. After an historical perspective on the development of these anionic reagents, this account describes their synthesis and their use as chiral NMR solvating, resolving and asymmetry-inducing reagents.

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confidence: 99%

Chiral hexacoordinated phosphates: From pioneering studies to modern uses in stereochemistry

Lacour

2010

Comptes Rendus. Chimie

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“…This outcome may also be because these two anions interact only weakly with cations [55], which may lead the imidazolium salts to generate NHCs more readily. Moreover, because PF 6 À and BF 4 À are non-coordinating anions, they will not coordinate to the palladium intermediate to block the reaction cycles.…”

Section: Resultsmentioning

confidence: 99%

Effect of counterions and central cores of tripodal imidazolium salts on palladium-catalyzed Suzuki–Miyaura cross-coupling reactions

Zhong

Wang

Guo

et al. 2011

Journal of Organometallic Chemistry

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“…[Et 3 NH][P(1,2-(O 2 C 6 H 4 ) 3 ] was isolated in 1963 and represents the first salt featuring a hexacoordinate organophosphate anion (i.e., [ A ] − ) . This catecholate system has evolved to the widely used chiral charge delocalized tris(tetrachlorobenzenediolato)phosphate, [ B ] − (R = Cl), and the related binol-derivative, [ C ] − . The tris(oxalato)phosphate anion, [ D ] − , has attracted attention as its lithium salt for potential application in lithium ion batteries .…”

Section: Introductionmentioning

confidence: 99%

Ammonium and Potassium Salts of a Hexacoordinate Phosphorus(V) Anion Featuring P–O and P–C Bonds

2018

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Ammonium and potassium salts featuring the chiral mer-[P(C6H4CO2)3]−, mer-[1]−, have been isolated. Specifically, treating phosphorane P(C6H4CO2)2(C6H4CO2H), 2, with N-containing bases [Nbase = PhNMe2, PhNH2, pyridine (py), isoquinoline, (−)-brucine, N(n-C8H17)3] afforded ammonium salts [NbaseH]+-mer-[1]−. Each compound was fully characterized spectroscopically, and four were subjected to X-ray crystallographic analysis. Salts were isolated with the racemic mixture of the mer-[1]− anion except in the case of [(−)-brucineH]-Λ-mer-[1], for which the crystal analyzed was enantiomerically pure. The potassium salt, K-mer-[1], was synthesized by treating 2 with KH. The solid-state structure of K-mer-[1] is a coordination polymer consisting of seven- and eight-coordinate K+ ions that are weakly bound by oxygen of either the racemic anion or the methanol solvent. Preliminary NMR and MS data for the formation of the Brønsted acid, H(DMF) n [1], has also been obtained. An estimate of the basicity of anion mer-[1]− was obtained from IR measurements of the N–H stretching frequency for [(n-C8H17)3NH]-mer-[1]. On the basis of these measurements, anion mer-[1]− was ranked similar to the classical weakly coordinating anion, [ClO4]−, in terms of its coordinating ability.

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New Trends in Hexacoordinated Phosphorus Chemistry

Cited by 24 publications

References 24 publications

Chiral hexacoordinated phosphates: From pioneering studies to modern uses in stereochemistry

Chiral hexacoordinated phosphates: From pioneering studies to modern uses in stereochemistry

Effect of counterions and central cores of tripodal imidazolium salts on palladium-catalyzed Suzuki–Miyaura cross-coupling reactions

Ammonium and Potassium Salts of a Hexacoordinate Phosphorus(V) Anion Featuring P–O and P–C Bonds

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