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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 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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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
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Groups of proteins may form a complex where each protein in this complex has a different role in the overall execution of the complex’s function. Often some of the proteins in the complex can be replaced by a closely related variant to give a complex that contains many of the same components yet is functionally distinct.
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A Continuous-flow Photocatalytic Reactor for the Precisely Controlled Deposition of Metallic Nanoparticles
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Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow.

Clémentine Minozzi1, Jean-Christophe Grenier-Petel1, Shawn Parisien-Collette1

  • 1Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.

Beilstein Journal of Organic Chemistry
|December 1, 2018
PubMed
Summary
This summary is machine-generated.

A novel copper-based photocatalyst efficiently converts alcohols to bromides and carboxylic acids to anhydrides. This photoredox Appel-type reaction is optimized for continuous flow, offering a scalable synthetic method.

Keywords:
Appelcontinuous flowcopperhalidesphotocatalysis

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Area of Science:

  • Organometallic Chemistry
  • Photocatalysis
  • Organic Synthesis

Background:

  • The Appel reaction is a crucial method for converting alcohols to alkyl halides.
  • Developing efficient and sustainable photocatalysts for organic transformations is an active area of research.
  • Copper complexes offer potential as earth-abundant and tunable photocatalysts.

Purpose of the Study:

  • To identify a novel copper-based photocatalyst for the Appel-type conversion of alcohols.
  • To explore the scope and limitations of the developed catalytic system.
  • To optimize the reaction for continuous flow conditions.

Main Methods:

  • Screening of 50 copper complexes to identify an active photocatalyst.
  • Photoredox catalysis utilizing the identified copper complex, Cu(tmp)(BINAP)BF4.
  • Optimization of reaction parameters and adaptation to a continuous flow microreactor system.

Main Results:

  • Cu(tmp)(BINAP)BF4 was identified as an effective photocatalyst for the Appel-type conversion.
  • The catalyst successfully transformed primary and secondary alcohols into their corresponding bromides.
  • The protocol also enabled the conversion of carboxylic acids to anhydrides and was optimized for continuous flow.

Conclusions:

  • A new copper-based photocatalyst, Cu(tmp)(BINAP)BF4, facilitates efficient photoredox Appel-type reactions.
  • The developed method offers a versatile route for synthesizing alkyl bromides and anhydrides.
  • Continuous flow optimization demonstrates the potential for scalable and sustainable chemical synthesis.