Hydroxymethyl bis(phosphines) and their palladium(II) and platinum(II) complexes formed via biphasic reactions. Crystal structure of [Pd{(HOH2C)2PC6H4P(CH2OH)2}2]Cl2

Reddy, V. Sreenivasa; Katti, Kattesh V.; Barnes, Charles L.

doi:10.1039/dt9960001301

Cited by 33 publications

(32 citation statements)

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“…A similar observation was recently made for the reactions of bis(phosphines) L6 and L7 with latetransition-metal precursors to afford several water-soluble complexes of Pd" and Pt11. 23,24 The rhenium(v) complexes 1-4 are stable in aqueous media for several weeks. This remarkable kinetic inertness may be attributed to the high nucleophilicity of the phosphorus centres in the these diphosphine tetraphosphonate ligands (i.e., L'-L4).…”

mentioning

confidence: 99%

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Reddy¹,

Katti²,

Volkert³

1996

J. Chem. Soc., Dalton Trans.

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confidence: 99%

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Reddy¹,

Katti²,

Volkert³

1996

J. Chem. Soc., Dalton Trans.

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“…In situ complexes were also formed with [Rh(COD)Cl] 2 for the hydrogenation of α-acetamidocinnamic acid 15 [13][14][15][16][17][18][19], (R,R)-21a, (S,S)-21b] and the hydrosilylation of acetophenone with diphenylsilane 16,17 (13)(14)(15)(16)(17)(18)(19). The catalytic reactions, their workup and analysis were performed following the procedures described in the literature.…”

Section: Results Of Catalytic Reactionsmentioning

confidence: 99%

Enantioselective Catalysis; 130: Optically Active Expanded Ligands Based on the trans-1,2-Substituted Cyclopentane Skeleton

Brunner

1999

Synthesis

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New expanded bisphosphane ligands with a chiral trans-1,2-substituted cyclopentane skeleton were prepared. Polyaldehydes were accessible by coupling optically active bisphosphane precursors with branched aryl bromides. Optically active expanded ligands were obtained by condensation of the aldehydes with chiral amines and amino alcohols. The optically active ligands were tested in several model reactions of enantioselective catalysis, including allylic alkylation, hydrogenation (adopted to the use of water), and hydrosilylation.

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“…14,15 Early reports on the formylation of 1,2-bis(phosphino)ethane and related analogues used harsh reaction conditions that involved employing high temperatures (>80°C) and longer durations under sealed setups. 16 It is important to recognize that phosphorus(III) hydrides are toxic and pyrophoric.…”

Section: Synthesis and Formylation Of Multinuclear Phosphinesmentioning

confidence: 99%

Design and Development of Functionalized Water-Soluble Phosphines: Catalytic and Biomedical Implications

et al. 1998

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Water is an environmentally (and biologically) benign solvent, and therefore, development of chemistry in aqueous media has long been a desirable goal for chemists. In particular, chemistry of water-soluble transition metal compounds has gained considerable prominence in recent years because of their usefulness in biphasic (aqueous-organic) catalysis 1 and biomedicine. 2 High solubility of transition metal compounds in water becomes a primary requirement in the design and development of catalysts for use under biphasic media because of the need for efficient separation and recovery of expensive transition metal catalysts (in aqueous media) from organic products. Additionally, the ability of specific transition metals to exert therapeutic (and diagnostic) influence on certain diseases has provided increased impetus in the development of new water-soluble and in vivo-stable transition metal compounds. 2,3 Of the various ligands available to stabilize specific oxidation states of transition metals and to produce aqueous soluble coordination compounds, functionalized phosphines are the most attractive class of ligands because of their versatile coordination chemistry. While aqueous soluble di-or trisulfonated arylphosphines, such as P(m-C 6 H 4 SO 3 Na) 3 , have largely been employed in the development of highly active water-soluble transition metal catalysts, 1 hydrophilic alkylphosphines are being highly sought after in order to gain specific structure-activity advantages in both catalytic and biomedical applications. In this context, the formylation of PH 3 , first reported by Hoffman et al., to produce tetrakis(hydroxymethyl)phosphonium chloride (THPC) has provided one of the earliest examples for the synthesis of hydrophilic alkylphosphines (Scheme 1). 4 Water-soluble tris(hydroxymethyl)phosphine (THP) was produced upon reaction of THPC with a suitable base (e.g., triethylamine or sodium bicarbonate buffer) (Scheme 1). 5 The transition metal chemistry of THP and other functionalized phosphines, over the years, has enabled the development of a wide spectrum of water-soluble transition metal/organometallic compounds for potential use in biphasic catalysis 5,6 and biomedicine. 7,8 The ease of transformation of P-H bonds into P-C bonds (as outlined in Scheme 1) is, undoubtedly, a synthetic novelty and the (hydroxymethyl)phosphorus compounds have provided a diverse range of chemical, catalytic, biological, environmental, and biomedical applications. 5-10 Despite the potential academic interest and scope for further technological advances, formylation reactions of functionalized phosphorus hydrides and, especially, of multinuclear phosphorus hydrides (i.e., bis-, tris-, or tetraphosphines) have, surprisingly, remained largely unexplored.It must be recognized that PH 3 , in its pure form, is an extremely hazardous chemical compound. It ignites in air at about 150°C and decomposes to produce phosphoric acid. 11 In its impure form, PH 3 gas is spontaneously inflammable at room temperature and this insta-

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Hydroxymethyl bis(phosphines) and their palladium(II) and platinum(II) complexes formed via biphasic reactions. Crystal structure of [Pd{(HOH2C)2PC6H4P(CH2OH)2}2]Cl2

Abstract: Hydroxymethyl bis(phosphines) and their palladium(n) and platinum(n) complexes formed via biphasic reactions. Crystal structure of ~~~~~0 ~2 2 , ~, ~~~~, o H ) , ) , l c12t

Cited by 33 publications

References 18 publications

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Enantioselective Catalysis; 130: Optically Active Expanded Ligands Based on the trans-1,2-Substituted Cyclopentane Skeleton

Design and Development of Functionalized Water-Soluble Phosphines: Catalytic and Biomedical Implications

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Hydroxymethyl bis(phosphines) and their palladium(II) and platinum(II) complexes formed via biphasic reactions. Crystal structure of [Pd{(HOH2C)2PC6H4P(CH2OH)2}2]Cl2

Abstract: Hydroxymethyl bis(phosphines) and their palladium(n) and platinum(n) complexes formed via biphasic reactions. Crystal structure of ~~~~~0 ~2 ~~2 ~~, ~, ~~~~, o H ) , ) , l c12t

Cited by 33 publications

References 18 publications

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Synthesis and characterization of dioxorhenium complexes derived from water-soluble diphosphine tetraphosphonates

Enantioselective Catalysis; 130: Optically Active Expanded Ligands Based on the trans-1,2-Substituted Cyclopentane Skeleton

Design and Development of Functionalized Water-Soluble Phosphines: Catalytic and Biomedical Implications

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Abstract: Hydroxymethyl bis(phosphines) and their palladium(n) and platinum(n) complexes formed via biphasic reactions. Crystal structure of ~~~~~0 ~2 2 , ~, ~~~~, o H ) , ) , l c12t