Chiral Iodotriptycenes: Synthesis and Catalytic Applications.
Nasim Khan1, Katsunori Itaya1, Thomas Wirth1
1School of Chemistry, Cardiff University, Park Place, Main Building, CF10 3AT, Cardiff, UK.
Chemistryopen
|July 13, 2022
Summary
New chiral iodotriptycenes were synthesized and tested as catalysts for oxidation reactions. Their catalytic performance and enantioselectivity were evaluated, revealing low enantioselectivities likely due to structural factors.
Area of Science:
- Organic Chemistry
- Catalysis
Background:
- Triptycenes are rigid molecular scaffolds with potential applications in catalysis.
- Iodotriptycenes offer unique structural features for designing novel catalysts.
Purpose of the Study:
- To synthesize new iodotriptycene derivatives, including chiral variants.
- To investigate the catalytic activity of these compounds in oxidative transformations.
- To evaluate the enantioselectivity of chiral iodotriptycene catalysts.
Main Methods:
- Synthesis of novel iodotriptycene compounds.
- Catalytic testing in oxidative reactions.
- Analysis of product enantioselectivity.
Main Results:
- Successful synthesis of new iodotriptycenes and their chiral derivatives.
- Demonstrated catalytic potential in oxidative transformations.
- Observed low enantioselectivities in reactions catalyzed by chiral iodotriptycenes.
Conclusions:
- The synthesized iodotriptycenes show promise as catalysts.
- Low enantioselectivity is attributed to the large distances between coordinating groups and iodine atoms in the catalyst structure.
More Related Videos
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
11.0K
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
12.6K
Related Concept Videos
02:05Prochirality
3.9K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
3.9K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.4K
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...
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...
3.4K
02:30Chirality in Nature
13.7K
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
13.7K
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
5.9K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
5.9K
01:17Thermal Electrocyclic Reactions: Stereochemistry
2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
02:25Chirality
25.1K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
25.1K