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Heterogeneous Catalysis01:22

Heterogeneous Catalysis

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Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Carbocations02:10

Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Intermolecular carbene S-H insertion catalysed by engineered myoglobin-based catalysts†.

Vikas Tyagi1, Rachel B Bonn1, Rudi Fasan1

  • 1Department of Chemistry, University of Rochester, 120 Trustee Rd, Rochester, New York 14627, USA.

Chemical Science
|June 24, 2015
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Researchers developed a biocatalytic method for synthesizing thioethers using engineered myoglobin. This novel approach efficiently creates carbon-sulfur bonds and allows for tunable enantioselectivity in the reaction.

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Area of Science:

  • Biocatalysis and Enzyme Engineering
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Thioether synthesis is crucial in pharmaceuticals and materials science.
  • Existing methods often require harsh conditions or toxic reagents.
  • Biocatalytic approaches offer sustainable alternatives for C-S bond formation.

Purpose of the Study:

  • To report the first biocatalytic strategy for thioether synthesis via intermolecular carbene S-H insertion.
  • To engineer myoglobin variants for efficient and selective C-S bond formation.
  • To investigate the mechanism and enantioselectivity of the biocatalytic reaction.

Main Methods:

  • Engineered variants of sperm whale myoglobin were created.
  • Catalysis of carbene S-H insertion reactions with various mercaptans and α-diazoesters.
  • Amino acid mutagenesis to tune enantioselectivity and mechanistic studies.

Main Results:

  • Engineered myoglobins efficiently catalyzed C-S bond formation with high conversions (60-99%).
  • High catalytic turnovers (1,100-5,400) were achieved across diverse substrates.
  • Myoglobin variants demonstrated tunable enantioselectivity, reaching up to 49% ee in asymmetric S-H insertions.

Conclusions:

  • Engineered myoglobin provides a versatile biocatalyst for thioether synthesis.
  • The developed method offers a sustainable and enantioselective route for C-S bond formation.
  • Mechanistic insights suggest a sulfonium ylide intermediate in the S-H insertion pathway.