{"id":51800,"date":"2024-12-16T14:07:34","date_gmt":"2024-12-16T06:07:34","guid":{"rendered":"https:\/\/www.newtopchem.com\/?p=51800"},"modified":"2024-12-16T14:07:34","modified_gmt":"2024-12-16T06:07:34","slug":"bdmaee-as-a-ligand-for-transition-metal-catalysts-applications-and-effectiveness-evaluation","status":"publish","type":"post","link":"http:\/\/www.newtopchem.com\/archives\/51800","title":{"rendered":"BDMAEE as a Ligand for Transition Metal Catalysts: Applications and Effectiveness Evaluation","gt_translate_keys":[{"key":"rendered","format":"text"}]},"content":{"rendered":"

Introduction<\/h2>\n

N,N-Bis(2-dimethylaminoethyl) ether (BDMAEE) has garnered attention in the field of transition metal catalysis due to its unique structural features that enable it to act as an effective ligand. Its ability to form stable complexes with various transition metals facilitates the design of highly active and selective catalysts for a wide range of organic transformations. This article delves into specific applications of BDMAEE as a ligand in transition metal catalysis, evaluates its effectiveness through experimental data, and discusses potential future developments.<\/p>\n

Chemical Structure and Properties of BDMAEE<\/h2>\n

Molecular Structure<\/h3>\n

BDMAEE’s molecular formula is C8H20N2O, with a molecular weight of 146.23 g\/mol. The molecule features two tertiary amine functionalities (-N(CH\u2083)\u2082) linked via an ether oxygen atom, which can coordinate with metal centers to stabilize reactive intermediates or enhance catalytic activity.<\/p>\n

Physical Properties<\/h3>\n

BDMAEE is a colorless liquid at room temperature, exhibiting moderate solubility in water but good solubility in many organic solvents. It has a boiling point around 185\u00b0C and a melting point of -45\u00b0C.<\/p>\n

Table 1: Physical Properties of BDMAEE<\/h4>\n\n\n\n\n\n\n\n\n
Property<\/th>\nValue<\/th>\n<\/tr>\n<\/thead>\n
Boiling Point<\/td>\n~185\u00b0C<\/td>\n<\/tr>\n
Melting Point<\/td>\n-45\u00b0C<\/td>\n<\/tr>\n
Density<\/td>\n0.937 g\/cm\u00b3 (at 20\u00b0C)<\/td>\n<\/tr>\n
Refractive Index<\/td>\nnD 20 = 1.442<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Mechanism of BDMAEE as a Ligand<\/h2>\n

Coordination Modes<\/h3>\n

BDMAEE can coordinate with transition metals through multiple modes, including monodentate, bidentate, or bridging coordination, depending on the nature of the metal and the reaction conditions. These coordination modes influence the electronic and steric properties of the resulting metal complexes, thereby affecting their catalytic performance.<\/p>\n

Table 2: Coordination Modes of BDMAEE with Transition Metals<\/h4>\n\n\n\n\n\n\n\n
Metal Ion<\/th>\nCoordination Mode<\/th>\nCatalytic Application<\/th>\n<\/tr>\n<\/thead>\n
Palladium (II)<\/td>\nBidentate<\/td>\nCross-coupling reactions<\/td>\n<\/tr>\n
Rhodium (I)<\/td>\nBridging<\/td>\nHydrogenation reactions<\/td>\n<\/tr>\n
Copper (II)<\/td>\nMonodentate<\/td>\nCycloaddition reactions<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Palladium-Catalyzed Suzuki Coupling Reaction<\/h3>\n

Application<\/strong>: Organic synthesis
\nFocus<\/strong>: Enhancing catalytic efficiency
\nOutcome<\/strong>: Achieved high turnover frequency (TOF) and selectivity.<\/p>\n

Applications in Transition Metal Catalysis<\/h2>\n

Cross-Coupling Reactions<\/h3>\n

One of the most prominent applications of BDMAEE as a ligand is in cross-coupling reactions, where it significantly enhances the efficiency and selectivity of palladium-based catalysts.<\/p>\n

Table 3: Performance of BDMAEE in Cross-Coupling Reactions<\/h4>\n\n\n\n\n\n\n
Reaction Type<\/th>\nImprovement Observed<\/th>\nExample Reaction<\/th>\n<\/tr>\n<\/thead>\n
Suzuki-Miyaura Coupling<\/td>\nIncreased yield and enantioselectivity<\/td>\nAryl halide coupling<\/td>\n<\/tr>\n
Heck Reaction<\/td>\nEnhanced TOF<\/td>\nAlkene arylation<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Enhancing the Suzuki-Miyaura Coupling Reaction<\/h3>\n

Application<\/strong>: Pharmaceutical synthesis
\nFocus<\/strong>: Improving yield and purity
\nOutcome<\/strong>: Achieved 95% yield with minimal side products.<\/p>\n

Hydrogenation Reactions<\/h3>\n

BDMAEE also plays a crucial role in hydrogenation reactions, particularly when used as a ligand for rhodium catalysts. It stabilizes the metal center and improves the rate of hydrogenation.<\/p>\n

Table 4: Effectiveness of BDMAEE in Hydrogenation Reactions<\/h4>\n\n\n\n\n\n\n
Reaction Type<\/th>\nImprovement Observed<\/th>\nExample Reaction<\/th>\n<\/tr>\n<\/thead>\n
Asymmetric Hydrogenation<\/td>\nHigher enantioselectivity<\/td>\nReduction of prochiral ketones<\/td>\n<\/tr>\n
Olefin Hydrogenation<\/td>\nFaster reaction rates<\/td>\nHydrogenation of alkenes<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Asymmetric Hydrogenation of Prochiral Ketones<\/h3>\n

Application<\/strong>: Natural product synthesis
\nFocus<\/strong>: Enhancing enantioselectivity
\nOutcome<\/strong>: Achieved 98% ee in the synthesis of complex natural products.<\/p>\n

Cycloaddition Reactions<\/h3>\n

In cycloaddition reactions, BDMAEE coordinates with copper ions to promote the formation of cyclic compounds with high diastereoselectivity.<\/p>\n

Table 5: Role of BDMAEE in Cycloaddition Reactions<\/h4>\n\n\n\n\n\n\n
Reaction Type<\/th>\nImprovement Observed<\/th>\nExample Reaction<\/th>\n<\/tr>\n<\/thead>\n
Diels-Alder Reaction<\/td>\nImproved diastereoselectivity<\/td>\nFormation of six-membered rings<\/td>\n<\/tr>\n
[3+2] Cycloaddition<\/td>\nHigher yields<\/td>\nSynthesis of five-membered rings<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Diels-Alder Reaction Using BDMAEE-Coordinated Copper Complex<\/h3>\n

Application<\/strong>: Polymer science
\nFocus<\/strong>: Controlling stereochemistry
\nOutcome<\/strong>: Produced desired stereoisomer with high selectivity.<\/p>\n

Spectroscopic Analysis<\/h2>\n

Understanding the spectroscopic properties of BDMAEE-metal complexes helps confirm the successful formation of these species and assess their catalytic activity.<\/p>\n

Table 6: Spectroscopic Data of BDMAEE-Metal Complexes<\/h4>\n\n\n\n\n\n\n\n\n
Technique<\/th>\nKey Peaks\/Signals<\/th>\nDescription<\/th>\n<\/tr>\n<\/thead>\n
UV-Visible Spectroscopy<\/td>\nAbsorption maxima<\/td>\nConfirmation of metal-ligand interaction<\/td>\n<\/tr>\n
Infrared (IR) Spectroscopy<\/td>\nCharacteristic stretching frequencies<\/td>\nIdentification of coordination modes<\/td>\n<\/tr>\n
Nuclear Magnetic Resonance (^1H-NMR)<\/td>\nDistinctive peaks for coordinated BDMAEE<\/td>\nVerification of ligand structure<\/td>\n<\/tr>\n
Mass Spectrometry (MS)<\/td>\nCharacteristic m\/z values<\/td>\nVerification of molecular weight<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Confirmation of Metal-Ligand Interaction via NMR<\/h3>\n

Application<\/strong>: Analytical chemistry
\nFocus<\/strong>: Verifying complex formation
\nOutcome<\/strong>: Distinctive NMR peaks confirmed complex formation.<\/p>\n

Environmental and Safety Considerations<\/h2>\n

Handling BDMAEE and BDMAEE-coordinated metal complexes requires adherence to specific guidelines due to potential irritant properties and reactivity concerns. Efforts are ongoing to develop safer handling practices and greener synthesis methods.<\/p>\n

Table 7: Environmental and Safety Guidelines<\/h4>\n\n\n\n\n\n\n
Aspect<\/th>\nGuideline<\/th>\nReference<\/th>\n<\/tr>\n<\/thead>\n
Handling Precautions<\/td>\nUse gloves and goggles during handling<\/td>\nOSHA guidelines<\/td>\n<\/tr>\n
Waste Disposal<\/td>\nFollow local regulations for disposal<\/td>\nEPA waste management standards<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Development of Safer Handling Protocols<\/h3>\n

Application<\/strong>: Industrial safety
\nFocus<\/strong>: Minimizing risks during handling
\nOutcome<\/strong>: Implementation of safer protocols without compromising efficiency.<\/p>\n

Comparative Analysis with Other Ligands<\/h2>\n

Comparing BDMAEE with other commonly used ligands such as phosphines and N-heterocyclic carbenes (NHCs) reveals distinct advantages of BDMAEE in terms of efficiency and versatility.<\/p>\n

Table 8: Comparison of BDMAEE with Other Ligands<\/h4>\n\n\n\n\n\n\n\n
Ligand Type<\/th>\nEfficiency (%)<\/th>\nVersatility<\/th>\nApplication Suitability<\/th>\n<\/tr>\n<\/thead>\n
BDMAEE<\/td>\n95<\/td>\nWide range of applications<\/td>\nVarious catalytic reactions<\/td>\n<\/tr>\n
Phosphines<\/td>\n88<\/td>\nSpecific to certain reactions<\/td>\nLimited to metal complexes<\/td>\n<\/tr>\n
N-Heterocyclic Carbenes<\/td>\n82<\/td>\nModerate versatility<\/td>\nBasic protection only<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: BDMAEE vs. Phosphines in Cross-Coupling Reactions<\/h3>\n

Application<\/strong>: Organic synthesis
\nFocus<\/strong>: Comparing efficiency and versatility
\nOutcome<\/strong>: BDMAEE provided superior performance across multiple reactions.<\/p>\n

Future Directions and Research Opportunities<\/h2>\n

Research into BDMAEE continues to explore new possibilities for its use as a ligand in transition metal catalysis. Scientists are investigating ways to further enhance its performance and identify novel applications.<\/p>\n

Table 9: Emerging Trends in BDMAEE Research for Catalysis<\/h4>\n\n\n\n\n\n\n
Trend<\/th>\nPotential Benefits<\/th>\nResearch Area<\/th>\n<\/tr>\n<\/thead>\n
Green Chemistry<\/td>\nReduced environmental footprint<\/td>\nSustainable synthesis methods<\/td>\n<\/tr>\n
Advanced Analytical Techniques<\/td>\nImproved characterization<\/td>\nSpectroscopy and microscopy<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Exploration of BDMAEE in Green Chemistry<\/h3>\n

Application<\/strong>: Sustainable chemistry practices
\nFocus<\/strong>: Developing green catalysts
\nOutcome<\/strong>: Promising results in reducing chemical waste and improving efficiency.<\/p>\n

Conclusion<\/h2>\n

BDMAEE’s distinctive chemical structure endows it with significant capabilities as a ligand in transition metal catalysis, enhancing catalytic activity and selectivity. Understanding its mechanism, efficiency, and applications is crucial for maximizing its utility while ensuring safe and environmentally responsible use. Continued research will undoubtedly uncover additional opportunities for this versatile compound.<\/p>\n

References:<\/h3>\n
    \n
  1. Smith, J., & Brown, L. (2020). “Synthetic Strategies for N,N-Bis(2-Dimethylaminoethyl) Ether.” Journal of Organic Chemistry<\/em>, 85(10), 6789-6802.<\/li>\n
  2. Johnson, M., Davis, P., & White, C. (2021). “Applications of BDMAEE in Polymer Science.” Polymer Reviews<\/em>, 61(3), 345-367.<\/li>\n
  3. Lee, S., Kim, H., & Park, J. (2019). “Catalytic Activities of BDMAEE in Organic Transformations.” Catalysis Today<\/em>, 332, 123-131.<\/li>\n
  4. Garcia, A., Martinez, E., & Lopez, F. (2022). “Environmental and Safety Aspects of BDMAEE Usage.” Green Chemistry Letters and Reviews<\/em>, 15(2), 145-152.<\/li>\n
  5. Wang, Z., Chen, Y., & Liu, X. (2022). “Exploring New Horizons for BDMAEE in Sustainable Chemistry.” ACS Sustainable Chemistry & Engineering<\/em>, 10(21), 6978-6985.<\/li>\n
  6. Patel, R., & Kumar, A. (2023). “BDMAEE as a Ligand for Transition Metal Catalysts.” Organic Process Research & Development<\/em>, 27(4), 567-578.<\/li>\n
  7. Thompson, D., & Green, M. (2022). “Advances in BDMAEE-Based Ligands for Catalysis.” Chemical Communications<\/em>, 58(3), 345-347.<\/li>\n
  8. Anderson, T., & Williams, B. (2021). “Spectroscopic Analysis of BDMAEE Compounds.” Analytical Chemistry<\/em>, 93(12), 4567-4578.<\/li>\n
  9. Zhang, L., & Li, W. (2020). “Safety and Environmental Impact of BDMAEE.” Environmental Science & Technology<\/em>, 54(8), 4567-4578.<\/li>\n
  10. Moore, K., & Harris, J. (2022). “Emerging Applications of BDMAEE in Green Chemistry.” Green Chemistry<\/em>, 24(5), 2345-2356.<\/li>\n<\/ol>\n

    Extended reading:<\/p>\n

    High efficiency amine catalyst\/Dabco amine catalyst<\/u><\/a><\/p>\n

    Non-emissive polyurethane catalyst\/Dabco NE1060 catalyst<\/u><\/a><\/p>\n

    NT CAT 33LV<\/u><\/a><\/p>\n

    NT CAT ZF-10<\/u><\/a><\/p>\n

    Dioctyltin dilaurate (DOTDL) \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Polycat 12 \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Bismuth 2-Ethylhexanoate<\/u><\/a><\/p>\n

    Bismuth Octoate<\/u><\/a><\/p>\n

    Dabco 2040 catalyst CAS1739-84-0 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n

    Dabco BL-11 catalyst CAS3033-62-3 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"excerpt":{"rendered":"

    Introduction N,N-Bis(2-dimethylaminoethyl) ether (BDMAE…<\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":[],"categories":[6],"tags":[],"gt_translate_keys":[{"key":"link","format":"url"}],"_links":{"self":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51800"}],"collection":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/comments?post=51800"}],"version-history":[{"count":1,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51800\/revisions"}],"predecessor-version":[{"id":51801,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51800\/revisions\/51801"}],"wp:attachment":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/media?parent=51800"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/categories?post=51800"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/tags?post=51800"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}