Palladium and Platinum Complexes with a β-Cyclodextrin-Functionalized Phosphine Ligand

Yang, Chuluo; Cheung, Yuk King; Yao, Junzhi; Wong, Yiu‐Tung; Jia, Guochen

doi:10.1021/om000634e

Cited by 19 publications

(12 citation statements)

References 45 publications

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“…Yield 0.31 g, 21%; mp 189 ЊC 1. H NMR (DMF-d 7 ): δ 3.58 (s, 4H, CH 2 ), 4.10 (dd, 2 J HH = 15.1 Hz, 2 J PH = 10.9 Hz, 8H, P-CH e -N), 6.10 (d,3 J HH = 8.4 Hz, 8H, o-H in N-C 6 H 4 ),6.87 (d,3 J HH = 8.4 Hz, 8H, m-H in N-C 6 H 4 ), 7 24.…”

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confidence: 99%

Self-assembly of novel macrocyclic aminomethylphosphines with hydrophobic intramolecular cavities

et al. 2004

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Novel macroheterocyclic tetraphosphines, namely, 1,1',5,5'-bis(arylene)-bis(1,5-diaza-3,7-diphosphacyclooctanes) 2-6, were obtained without the use of high-dilution techniques or any matrix by the reaction of bis(hydroxymethyl)organylphosphines with primary aromatic diamines containing two p-phenylene fragments linked by various one-atom bridges in a molecular self-assembly process. The structures of 4, 5 and 6 were investigated by X-ray crystal structure analyses. The macrocyclic cavities can be described as a truncated rhombohedral prism with side faces formed by phenylene rings and 1,5-diaza-3,7-diphosphacyclooctanes in the truncated acute angles. In the crystals of these macrocycles, solvating DMF molecules are present, and a methyl group from each of two DMF molecules penetrates the macrocyclic cavities of 4 and 5 from either side, whereas only one disordered molecule of DMF penetrates the cavity of macrocycle 6. Different types of crystal packing are observed for the P-benzyl-substituted compounds 4 and 5 and for the P-mesityl-substituted compound 6: for 4 and 5 the formation of alternating layers containing the macrocycles and the DMF molecules is observed, in which the cavities of the macrocyclic molecules form channels and the DMF molecules are located in the centers of the channels; in the crystal of 6, six molecules are arranged around the 3 axis in the fashion of a six-bladed propeller.

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confidence: 99%

Self-assembly of novel macrocyclic aminomethylphosphines with hydrophobic intramolecular cavities

et al. 2004

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“…[38][39][40] Note that large quantities of pure mono-6-O-tosyl-CD can only be obtained from β-CD, 41 and unsurprisingly, most monosubstituted, P(III)-containing CDs are β-CD derivatives. In some cases, the P(III) fragment was introduced after the tosyl group had been reacted with a nucleophile suitable for further functionalisation (typically sodium azide 42 or amines 43 ). Permethylated mono-6-O-tosyl-CDs offer more possibilities than their polyhydroxylated counterparts for the introduction of phosphine groups because these derivatives are compatible with strongly basic conditions and are easier to purify.…”

Section: Monofunctionalisationmentioning

confidence: 99%

“…This ligand was used for the preparation of the cationic pincer complexes [PdCl (23)]Cl, [PtCl (23)]Cl and [Pd(η 1allyl) (23)]Cl. 43 Due to the presence of a stereogenic nitrogen atom, two diastereomers formed upon complexation (1 : 1 ratio).…”

Section: Multidentate Ligandsmentioning

confidence: 99%

Cyclodextrin and phosphorus(iii): a versatile combination for coordination chemistry and catalysis

2015

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With the advent of efficient methods for functionalising cyclodextrins, the synthesis of a variety of cyclodextrin-based P(III) ligands has been made possible. Capable of acting both as first and second coordination sphere ligands towards various transition metals, these compounds have found many applications in homogeneous catalysis. This perspective article describes the different approaches that have been used to covalently associate the ubiquitous P(III) donor atom with a cyclodextrin cavity. In addition, special emphasis is placed on the influence the cyclodextrin receptor has on the coordination and catalytic properties of these cavity-shaped ligands.

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“…In addition, the metal can be coordinated and rendered water-soluble thanks to the phosphane moiety covalently attached to the CD platform. For twenty years, various CD-mono, di, tri or tetra-phosphanes have been described in the literature [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], but only some CD-functionalized by one or two phosphorous moieties were exploited in aqueous organometallic catalytic processes [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. Nevertheless, while their coordinating properties towards a transition metal and their catalytic properties were fully detailed, their mass transfer agent properties were much less discussed.…”

Section: Introductionmentioning

confidence: 99%

Phosphane-Based Cyclodextrins as Mass Transfer Agents and Ligands for Aqueous Organometallic Catalysis

et al. 2012

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The replacement of hazardous solvents and the utilization of catalytic processes are two key points of the green chemistry movement, so aqueous organometallic catalytic processes are of great interest in this context. Nevertheless, these processes require not only the use of water-soluble ligands such as phosphanes to solubilise the transition metals in water, but also the use of mass transfer agents to increase the solubility of organic substrates in water. In this context, phosphanes based on a cyclodextrin skeleton are an interesting alternative since these compounds can simultaneously act as mass transfer agents and as coordinating species towards transition metals. For twenty years, various cyclodextrin-functionalized phosphanes have been described in the literature. Nevertheless, while their coordinating properties towards transition metals and their catalytic properties were fully detailed, their mass transfer agent properties were much less discussed. As these mass transfer agent properties are directly linked to the availability of the cyclodextrin cavity, the aim of this review is to demonstrate that the nature of the reaction solvent and the nature of the linker between cyclodextrin and phosphorous moieties can deeply influence the recognition properties. In addition, the impact on the catalytic activity will be also discussed.

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Palladium and Platinum Complexes with a β-Cyclodextrin-Functionalized Phosphine Ligand

Cited by 19 publications

References 45 publications

Self-assembly of novel macrocyclic aminomethylphosphines with hydrophobic intramolecular cavities

Self-assembly of novel macrocyclic aminomethylphosphines with hydrophobic intramolecular cavities

Cyclodextrin and phosphorus(iii): a versatile combination for coordination chemistry and catalysis

Phosphane-Based Cyclodextrins as Mass Transfer Agents and Ligands for Aqueous Organometallic Catalysis

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