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Related Concept Videos

Elimination Reactions02:25

Elimination Reactions

14.6K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
14.6K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.5K
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...
3.5K
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

12.2K
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
12.2K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.1K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
10.1K
Sharpless Epoxidation02:57

Sharpless Epoxidation

4.4K
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...
4.4K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

12.6K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
12.6K

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Asymmetric Elimination Reaction on Chiral Metal Surfaces.

Samuel Stolz1,2, Martina Danese1, Marco Di Giovannantonio1

  • 1Nanotech@surfaces Laboratory, Empa - Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, Dübendorf, CH-8600, Switzerland.

Advanced Materials (Deerfield Beach, Fla.)
|October 6, 2021
PubMed
Summary

Chiral intermetallic PdGa surfaces enable asymmetric dehalogenation of 5-bromo-7-methylbenz(a)anthracene. This breakthrough demonstrates enantiospecific control for on-surface synthesis, achieving a record 46 K difference in debromination temperatures.

Keywords:
asymmetric catalysischiral materials, intermetallic compoundssurface chemistrysurface enantiomers

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Area of Science:

  • Surface Science
  • Asymmetric Synthesis
  • Materials Chemistry

Background:

  • Enantiopure materials are crucial for nonlinear optics and asymmetric synthesis.
  • Dehalogenation is a key reaction step in many chemical processes.
  • Controlling enantioselectivity on surfaces is a significant challenge.

Purpose of the Study:

  • To investigate asymmetric dehalogenation of prochiral 5-bromo-7-methylbenz(a)anthracene (BMA).
  • To explore the use of chiral, intermetallic PdGa{111} surfaces for enantioselective reactions.
  • To demonstrate enantiospecific control in on-surface synthesis.

Main Methods:

  • Utilizing temperature-programmed X-ray photoelectron spectroscopy (TPXPS).
  • Employing scanning probe microscopy (SPM).
  • Conducting density functional theory (DFT) calculations.

Main Results:

  • Achieved asymmetric halogen elimination on PdGa{111} surfaces.
  • Observed an unprecedented 46 K difference in debromination temperatures for BMA enantiomers.
  • Demonstrated significant dependence of dehalogenation temperature on surface atomic termination, indicating a pronounced ensemble effect.

Conclusions:

  • Chiral PdGa{111} surfaces facilitate enantiospecific control in dehalogenation reactions.
  • Intrinsically chiral crystals are promising for asymmetric on-surface synthesis.
  • The findings open new avenues for designing chiral catalysts for surface-based reactions.