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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.0K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.0K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

11.8K
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.
The hydrogenation process takes place on the...
11.8K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Dynamic boron-doping switched chitin-based single-atom Pt catalyst for chemo-selective hydrogenation.

Yan Li1, Lijun Lu1, Xueyu Jiang1,2

  • 1College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan, P. R. China.

Nature Communications
|March 7, 2025
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Summary

This study presents a cost-effective method for creating novel chitin-derived single-atom platinum catalysts (SS-Pt-CSNs). These advanced catalysts demonstrate superior selectivity and efficiency in hydrogenation reactions, promoting sustainable waste-to-wealth strategies.

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Area of Science:

  • Materials Science
  • Catalysis
  • Green Chemistry

Background:

  • Biomass valorization aligns with the 'waste-to-wealth' concept crucial for sustainability.
  • Prioritizing natural polymers for value-added materials is essential.
  • Developing efficient catalysts from renewable resources is a key challenge.

Purpose of the Study:

  • To develop an economical method for preparing chitin-derived supramolecular nanowires-stabilized single-atom sites Pt catalysts (SS-Pt-CSNs).
  • To investigate the catalytic performance and structural characteristics of these novel catalysts.

Main Methods:

  • Facile and economical synthesis of SS-Pt-CSNs using chitin.
  • Comprehensive characterization of the catalyst structure and composition.
  • Evaluation of catalytic performance in chemo-selective hydrogenation reactions.

Main Results:

  • Successfully prepared SS-Pt-CSNs with single-atom Pt coordinated to an organic supramolecular entity.
  • Achieved excellent catalytic performance for chemo-selective hydrogenation with >90:1 selectivity.
  • Recorded a high turnover number (TON) of 121,350.
  • Identified empty Pt coordination sites and dynamic B-doping as key factors for efficiency.

Conclusions:

  • SS-Pt-CSNs exhibit hybrid characteristics of homogeneous and heterogeneous catalysts.
  • The developed catalysts offer exceptional efficiency and selectivity for hydrogenation.
  • This work advances biomass valorization and sustainable catalysis.