New Catalysts and Conditions for a CH Insertion Reaction Identified by High Throughput Catalyst Screening

Burgess, Kevin; Lim, H.; Porte, Alexander M.; Sulikowski, Gary A.

doi:10.1002/anie.199602201

Cited by 217 publications

(104 citation statements)

References 12 publications

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“…Many different approaches have been reported to address this problem. Methods such as GC [23,26,28,29], GLC [27], HPLC [30][31][32], UV/Vis [33,34], electrospray ionization MS [35,36], IR thermography [37,38], fluorescence [39], and visible color change [40,41] have been used to assay for product formation.…”

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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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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“…Combinatorial chemistry is not yet widely used to accelerate the development of new catalysts [145][146][147][148][149]. Since 1995 some attempts have been made to apply combinatorial strategies to problems in stereoselective homogeneous catalysis, mainly by U.S. groups.…”

Section: Combinatorial Chemistry and Catalysismentioning

confidence: 99%

Combinatorial Chemistry

Tiebes

Peters

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Concept of Combinatorial Chemistry 3. Methods and Techniques of Combinatorial Synthesis 3.1. Synthetic Strategies Towards Combinatorial Libraries 3.1.1. Split ‐ Pool Synthesis Towards Combinatorial Libraries 3.1.1.1. Techniques using Resin Beads 3.1.1.2. Tea‐Bag Method 3.1.2. Parallel Synthesis Towards Combinatorial Libraries 3.1.2.1. Reaction Apparatus using Resin Beads 3.1.2.2. Multipin Technique 3.1.2.3. Spatially Addressable Parallel Synthesis on Silica Wafer 3.1.3. Reagent Mixture Synthesis Towards Combinatorial Libraries 3.2. Synthetic Methodology for Organic Library Construction 3.2.1. Solid‐Phase Organic Synthesis 3.2.1.1. Solid Support, Linker, and Cleavage Strategies 3.2.1.2. Reaction Portfolio 3.2.2. Synthesis in Solution and Liquid‐Phase Synthesis 4. Characterization of Combinatorial Libraries 4.1. Analytical Characterization 4.2. Hit Identification in Combinatorial Libraries by High‐Throughput Screening 4.2.1. Strategies for Libraries of Compound Mixtures 4.2.1.1. On‐Bead Screening 4.2.1.2. Deconvolution 4.2.1.2.1. Iterative Deconvolution 4.2.1.2.2. Deconvolution by Positional Scanning 4.2.1.2.3. Deconvolution by Orthogonal Libraries 4.2.1.3. Encoding 4.2.1.4. Multiple Cleavable Linkers 4.2.2. Strategies for Libraries of Separate Single Compounds 4.2.3. Conclusion 5. Automation and Data Processing 5.1. Synthesis Automation and Data Processing 5.2. Automated Purification 6. Library Design and Diversity Assessment 6.1. Diversity Assessment for Selection of Building Blocks or Compound 6.2. Iterative Optimization Methods 7. Economic Aspects and Industrial Case Studies 8. Further Developments 8.1. Combinatorial Chemistry and Catalysis 8.2. Combinatorial Chemistry and Material Science

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“…First, there have been major advances in areas like combinatorial synthesis (42,43). This has led to the development of highthroughput catalyst screens that may prove useful if the small-scale reactions can be generalized to preparative scale chemistry (44). It is anticipated that many groups will develop approaches to combinatorial development and assay of catalysts once creative approaches to multiplexed screening assays are developed.…”

Section: Soluble Polymer-bound Catalysts and Substratesmentioning

confidence: 99%