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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
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Ir0/graphdiyne atomic interface for selective epoxidation.

Zhiqiang Zheng1, Lu Qi1, Yaqi Gao1

  • 1Shandong Provincial Key Laboratory for Science of Material Creation and Energy Conversion, Science Center for Material Creation and Energy Conversion, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.

National Science Review
|July 10, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed novel zerovalent iridium on graphdiyne (Ir0/GDY) catalysts for efficient alkene epoxidation. This sustainable method produces styrene oxides with high selectivity and conversion under ambient conditions.

Keywords:
atom catalystatomic interfacegraphdiynehigh-performance conversionselective epoxidation

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Area of Science:

  • Catalysis
  • Materials Science
  • Electrochemistry

Background:

  • Selective alkene epoxidation is crucial for renewable chemical synthesis.
  • Developing efficient catalysts for ambient conditions remains a challenge.

Purpose of the Study:

  • To develop a novel catalyst for selective and efficient alkene epoxidation.
  • To investigate the use of zerovalent iridium atoms anchored on graphdiyne (Ir0/GDY) for electrocatalytic styrene epoxidation.

Main Methods:

  • Synthesis of highly dispersed zerovalent iridium atoms on graphdiyne (Ir0/GDY).
  • Electrocatalytic oxidation of styrene (ST) to styrene oxides (SO) in aqueous solutions.
  • Experimental characterization and density functional theory (DFT) calculations.

Main Results:

  • Ir0/GDY demonstrated high conversion efficiency (~100%), high SO selectivity (85.5%), and high Faradaic efficiency (55%).
  • The catalyst operates effectively at ambient temperatures and pressures.
  • DFT calculations confirmed the role of charge transfer and confinement effects in stabilizing Ir0 and promoting catalysis.

Conclusions:

  • Ir0/GDY is a highly effective catalyst for selective electrocatalytic epoxidation.
  • The unique electronic properties and structural stability of Ir0/GDY enable efficient alkene-to-epoxide conversion.
  • This work offers a new strategy for designing zerovalent metal atom catalysts for epoxidation reactions.