Hydrogen Bonding as a Construction Element for Bidentate Donor Ligands in Homogeneous Catalysis:  Regioselective Hydroformylation of Terminal Alkenes

Breit, Bernhard; Seiche, Wolfgang

doi:10.1021/ja0348997

Cited by 293 publications

(169 citation statements)

References 4 publications

(4 reference statements)

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“…In the presence of transition metal ions 6-diphenylphosphinopyridone forms an H-bridged associate with its own tautomer. Bidentate character of this self-organized molecule was established both in solution (NMR) and in solid phase (X-ray) [5].…”

Section: Introductionmentioning

confidence: 99%

Two in one: Charged tertiary phosphines held together by ionic or covalent interactions as bidentate phosphorus ligands for synthesis of half-sandwich Ru(II)-complexes

et al. 2013

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Ion pairs containing N-substituted derivatives of 1,3,5-triaza-7-phosphaadamantane (pta-R; R= benzyl, butyl, hexyl) as cations and monosulfonated triphenylphosphine (mtppms) as anion were synthetized and characterized (including X-ray diffraction, too). These ion pairs act as bidentate phosphorus ligands in reactions with [(η 6 -C 10 H 14 )RuCl 2 ] 2 , yielding mononuclear or dinuclear half sandwich Ru(II) complexes. A bisphosphine 3 of good watersolubility was synthesized in reaction of pta with 1,4-bis(chloromethyl)benzene and used for the synthesis of the water-soluble dinuclear complex [{(η 6 -C 10 H 14 )RuCl 2 } 2 (μ-3)]Cl 2 .

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Section: Introductionmentioning

confidence: 99%

Two in one: Charged tertiary phosphines held together by ionic or covalent interactions as bidentate phosphorus ligands for synthesis of half-sandwich Ru(II)-complexes

et al. 2013

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“…138 The most prominent example of such supramolecular self-assembling ligands is the 6-diphenylphosphinopyridin-2-(1H)-one (6-DPPon) system which proved to give rise to an extremely active hydroformylation catalyst for terminal alkenes enabling the reactions to be carried out at ambient pressure and room temperature.…”

mentioning

confidence: 99%

Computational aspects of hydroformylation

Kégl

2015

RSC Adv.

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The influence of transition metal complexes as catalysts upon the activity and selectivity of hydroformylation reactions has been extensively investigated during the last decades. Nowadays computational chemistry is an indispensable tool for elucidation of reaction mechanisms and for understanding the various aspects which govern the outcome of catalytic reactions. This review attempts to survey the recent literature concerning computational studies on hydroformylation and theoretical coordination chemistry results related to hydroformylation.

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“…For example, means to predict the selectivity provided by transition metal catalyst are lacking, and therefore high throughput screening of libraries of catalysts is still the most powerful method to find catalyst systems with desired selectivities. Indeed, we and others have introduced supramolecular ways to make transition metal catalysts and used the building block approach to create large libraries of related catalysts, some of which show unrivaled selectivities (5)(6)(7)(8)(9).…”

mentioning

confidence: 99%

Self-assembled biomimetic [2Fe2S]-hydrogenase-based photocatalyst for molecular hydrogen evolution

Kluwer

Kapre²,

Hartl³

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

211

137

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The large-scale production of clean energy is one of the major challenges society is currently facing. Molecular hydrogen is envisaged as a key green fuel for the future, but it becomes a sustainable alternative for classical fuels only if it is also produced in a clean fashion. Here, we report a supramolecular biomimetic approach to form a catalyst that produces molecular hydrogen using light as the energy source. It is composed of an assembly of chromophores to a bis(thiolate)-bridged diiron ([2Fe2S]) based hydrogenase catalyst. The supramolecular building block approach introduced in this article enabled the easy formation of a series of complexes, which are all thoroughly characterized, revealing that the photoactivity of the catalyst assembly strongly depends on its nature. The active species, formed from different complexes, appears to be the [Fe 2(-pdt)(CO)4{PPh2(4-py)}2] (3) with 2 different types of porphyrins (5a and 5b) coordinated to it. The modular supramolecular approach was important in this study as with a limited number of building blocks several different complexes were generated.photocatalysis ͉ self-assembly ͉ supramolecular chemistry ͉ metalloporphyrin chromophore ͉ Stern-Volmer plot S upramolecular chemistry, defined by Nobel Prize Laureate Jean-Marie Lehn as the ''chemistry beyond the molecule,'' has changed the way we look at molecules (1). Besides exploring reactivity of molecules, interaction between molecules has become of dominant importance as it provides new means of controlling properties of chemical systems. Supramolecular chemistry has rapidly evolved into a mature field, and the implementation of supramolecular strategies has resulted in breakthroughs in several disciplines (2-4). The reversible character of noncovalent chemistry gives rise to concepts such as adaptation and self-correction, creating fundamentally different system properties compared with traditional covalent strategies. The modular character associated with the building block approach in supramolecular chemistry provides an easy strategy to generate large libraries of analogous structures of nanosize dimension. Such libraries are of interest in research areas where accurate prediction of particular properties of chemical systems is inadequate or impossible. For example, means to predict the selectivity provided by transition metal catalyst are lacking, and therefore high throughput screening of libraries of catalysts is still the most powerful method to find catalyst systems with desired selectivities. Indeed, we and others have introduced supramolecular ways to make transition metal catalysts and used the building block approach to create large libraries of related catalysts, some of which show unrivaled selectivities (5-9).Stimulated by these exciting results, we were wondering whether supramolecular strategies could also provide solutions to other challenges in catalysis. One of the greatest challenges our society is currently facing is the large-scale production of clean energy (10). Molecular hydrogen is e...

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Hydrogen Bonding as a Construction Element for Bidentate Donor Ligands in Homogeneous Catalysis: Regioselective Hydroformylation of Terminal Alkenes

Cited by 293 publications

References 4 publications

Two in one: Charged tertiary phosphines held together by ionic or covalent interactions as bidentate phosphorus ligands for synthesis of half-sandwich Ru(II)-complexes

Two in one: Charged tertiary phosphines held together by ionic or covalent interactions as bidentate phosphorus ligands for synthesis of half-sandwich Ru(II)-complexes

Computational aspects of hydroformylation

Self-assembled biomimetic [2Fe2S]-hydrogenase-based photocatalyst for molecular hydrogen evolution

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