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Coupled Reactions01:17

Coupled Reactions

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Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
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Acids, Bases and Neutralization Reactions03:26

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An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
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Acids, Bases and Neutralization Reactions01:27

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Acids and bases play several important roles in biology. The pH of a biological system can significantly impact the function of biological molecules, including enzymes, proteins, and nucleic acids. For example, enzymes have optimal pH ranges for their activity, and changes in pH can denature or alter their structure, affecting their function. Acids and bases also play a crucial role in cellular signaling and communication. The pH of the extracellular fluid around cells can influence the...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions.

Sebastian B Beil1,2, Timo Müller1, Sydney B Sillart1

  • 1Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.

Angewandte Chemie (International Ed. in English)
|January 11, 2018
PubMed
Summary
This summary is machine-generated.

Researchers discovered a new molybdenum anode system for dehydrogenative coupling reactions in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). This sustainable electrolytic method replaces stoichiometric reagents for broad arene conversion.

Keywords:
anodearene couplingelectrochemistrymolybdenumoxidative coupling

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Area of Science:

  • Electrochemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Dehydrogenative coupling of arenes often requires stoichiometric, high-valent molybdenum reagents.
  • Existing methods can be limited in scope and sustainability.

Purpose of the Study:

  • To develop a novel, powerful, and sustainable active anode system for dehydrogenative coupling.
  • To enable the use of electrolysis in place of stoichiometric reagents.

Main Methods:

  • Electrochemical investigation of a molybdenum anode in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP).
  • Characterization of the anode surface layer formed in HFIP.

Main Results:

  • A new active anode system operating in HFIP was discovered.
  • The molybdenum anode forms a compact, conductive, and electroactive layer of higher-valent molybdenum species in HFIP.
  • This system effectively replaces stoichiometric Mo(V) reagents.

Conclusions:

  • The developed electrolytic system offers a more sustainable alternative for dehydrogenative coupling of aryls.
  • The system demonstrates broad applicability for the conversion of activated arenes.