Reactive Dyes as a Method for Rapid Screening of Homogeneous Catalysts

Cooper, Alan C.; McAlexander, Lenore H.; Lee, Dong-Heon; Torres, Matthew T.; Crabtree, Robert H.

doi:10.1021/ja9818607

Cited by 93 publications

(42 citation statements)

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“…The combinatorial method entails the synthesis of large libraries of compounds, in which composition or processing conditions are systematically varied, followed by screening for a particular property of interest. Recently, this approach has been used with some success in the discovery of new catalysts [3][4][5][6], and sophisticated methods for rapid screening of catalyst libraries have now been developed [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Combinatorial discovery of bifunctional oxygen reduction — water oxidation electrocatalysts for regenerative fuel cells

2001

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Section: Introductionmentioning

confidence: 99%

Combinatorial discovery of bifunctional oxygen reduction — water oxidation electrocatalysts for regenerative fuel cells

2001

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“…Thinking that a visible light response might be appropriate for the initial work, we designed a reactive visible dye [43,44]. Conventional dyes consist of an electron donor linked to an electron-acceptor by an unreactive unsaturated link.…”

Section: Meoh + Co = Mecoohmentioning

confidence: 99%

Rapid screening and combinatorial methods in homogeneous organometallic catalysis

Loch

Crabtree

2001

Pure and Applied Chemistry

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Methods are discussed for rapid screening of soluble and polymer-bound homogeneous catalysts for activity. A polymer-bound phosphine library is synthesized, and a modular tridentate pincer CNC bis-carbene Pd complex is described. The possibility of C-bound His in metalloenzymes is raised.Homogeneous catalysis has much to offer Green Chemistry. By allowing reactions to occur at lower temperature and pressure, energy is saved. By enhancing selectivity, waste is avoided. Waste can even be essentially eliminated if catalysis allows atom-economic processes to be used. These are reactions like eq. 1 in which all the atoms of the reagents are incorporated into the product [1,2]. This particular rhodium-catalyzed reaction-the Monsanto Process-is a commercially important route to acetic acid [3]. In contrast, much conventional industrial chemistry still goes via reactions that produce stoichiometric amounts of inorganic salts or tainted water as byproducts. MeOH + CO = MeCOOH(1)For each new application, new homogeneous catalysts may well need to be identified and optimized, then understood mechanistically. Mechanization and computerization, now becoming more readily available and efficient, can help with all these goals. Combinatorial chemistry [4][5][6][7], together with rapid catalyst screening [8,9], has potential value in identification and optimization. The latest methods of computational and theoretical chemistry can give very valuable mechanistic information in ruling out otherwise plausible pathways and predicting structural information for transient species and transition states [10]. Here, we naturally discuss only the title topic, although by doing so we do not intend to detract from the importance of mechanistic understanding.The principles of combinatorial chemistry have been covered in several recent monographs and reviews [11][12][13][14][15][16]. In summary, the concept involves creating a large number of chemically distinct species-called a library-in a controlled way. This library is then assayed by a suitable rapid screening protocol to see if a desired response is elicited. The library members showing a good response, termed "hits", are then analyzed to determine the chemical structure responsible for the desired response.The field has its intellectual roots in an understanding of how the immune system works and in Merrifield's [17] approach to polypeptide synthesis. The immune system has the task of tagging foreign biomolecules to label them for attack. To do this, it creates a library of polypeptides of variable structure, then senses when one of these peptides by chance binds strongly to a foreign target, such as the surface of an invading bacterium, for example. The successful immune system peptide is then synthesized on a large scale to carry out its defense role in the body.

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“…An extra twist was provided for the detection of enantioselectivity of the catalysts: The array of reactants included the two different enantiomers of substrate, for which the catalysts showed drastically different activities. Crabtree and co-workers recognized the attractive features of color changes for parallel assay purposes and developed reactive dyes that contain an electron donor and acceptor linked by a reactive functionality such as C C. [20] When this functionality is changed during the catalytic reaction, for example, by hydrosilation, the electronic connection between the donor and acceptor groups is interrrupted, and the color of the dye fades (Figure 1). This elegant approach promises to be amenable to many other catalytic reactions.…”

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confidence: 99%

“…The dye changes its color from deep purple to light yellow following hydrosilation with a homogeneous catalyst within a few minutes. [20] Very different types of challenges await the practitioner of heterogeneous catalysis. While arrays of heterogeneous catalysts such as metal alloys or mixed oxides could be automatically constructed along the lines developed by Symyx and others (gas-phase deposition or liquid dosing), the assay of catalytic activity is nontrivial.…”

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confidence: 99%

Efficient Assays for Combinatorial Methods for the Discovery of Catalysts

Bein

1999

Angew. Chem. Int. Ed.

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The revolutionary developments in combinatorial approaches to pharmaceutical science are now being explored in such diverse areas as materials design and homogeneous and heterogeneous catalysis. The quest for more efficient and selective catalysts has created the desire to design parallel assays for catalytic activity in combinatorial studies. This contribution highlights some of the recent exciting developments in this area.

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Reactive Dyes as a Method for Rapid Screening of Homogeneous Catalysts

Cited by 93 publications

References 9 publications

Combinatorial discovery of bifunctional oxygen reduction — water oxidation electrocatalysts for regenerative fuel cells

Combinatorial discovery of bifunctional oxygen reduction — water oxidation electrocatalysts for regenerative fuel cells

Rapid screening and combinatorial methods in homogeneous organometallic catalysis

Efficient Assays for Combinatorial Methods for the Discovery of Catalysts

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