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Acid Halides to Esters: Alcoholysis01:12

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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Introduction
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Highly Active Cellulose-Supported Poly(hydroxamic acid)-Cu(II) Complex for Ullmann Etherification.

Choong Jian Fui1, Tang Xin Ting1, Mohd Sani Sarjadi1

  • 1Faculty of Science and Natural Resources, University Malaysia Sabah, 88400 Kota Kinabalu, Sabah, Malaysia.

ACS Omega
|March 22, 2021
PubMed
Summary
This summary is machine-generated.

A novel cellulose-supported copper(II) complex derived from pandanus was synthesized and effectively catalyzed Ullmann etherification reactions. This stable catalyst demonstrates excellent reusability for synthesizing valuable ethers.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Catalysis

Background:

  • Development of efficient and reusable catalysts is crucial for sustainable chemical synthesis.
  • Cellulose, a natural polymer, offers a sustainable support for catalyst immobilization.
  • Poly(hydroxamic acid) ligands can effectively chelate metal ions for catalytic applications.

Purpose of the Study:

  • To synthesize a novel cellulose-supported poly(hydroxamic acid)-Cu(II) complex.
  • To investigate the catalytic activity of the synthesized complex in Ullmann etherification.
  • To evaluate the stability and reusability of the catalyst.

Main Methods:

  • Graft copolymerization of methyl acrylate onto pandanus cellulose.
  • Conversion of the copolymer to poly(hydroxamic acid) ligand via Loosen rearrangement.
  • Immobilization of Cu(II) ions onto the ligand-supported cellulose.
  • Characterization using FTIR, FE-SEM, EDX, TEM, ICP-OES, TGA, XRD, and XPS.
  • Application in Ullmann etherification of aryl/benzyl halides with phenols.

Main Results:

  • Successful synthesis and characterization of the cellulose-supported Cu(II) complex (4).
  • The catalyst efficiently promoted Ullmann etherification, yielding ethers in excellent yields (70-99% for benzyl halides, 20-90% for aryl halides).
  • The catalyst exhibited high stability and was reused up to seven times without significant loss of activity.

Conclusions:

  • The synthesized pandanus cellulose-supported poly(hydroxamic acid)-Cu(II) complex is a highly active and reusable catalyst for Ullmann etherification.
  • This catalytic system offers a promising route for the commercial preparation of various ethers.
  • The synthetic approach holds potential for applications in natural product synthesis and medicinal chemistry.