A Tandem Catalysis for Isoindolinone Synthesis over Single-Atom Pd/TiO2 Catalyst
Jin Xie1, Jianian Cheng1, Junbao Peng1
1Key Laboratory of Advanced Catalysis, Gansu Province, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, China.
Angewandte Chemie (International Ed. in English)
|September 12, 2024
Summary
A novel single-atom palladium on titanium dioxide (Pd/TiO2) tandem catalyst efficiently synthesizes the isoindolinone (IIO) scaffold. This method offers a sustainable alternative for producing pharmaceutical building blocks.
Area of Science:
- Catalysis
- Materials Science
- Organic Synthesis
Background:
- The isoindolinone (IIO) scaffold is a vital structural motif in pharmaceutical development.
- Conventional synthesis methods for IIO scaffolds face challenges in efficiency and sustainability.
- Developing alternative, high-performance catalytic strategies is crucial for pharmaceutical synthesis.
Purpose of the Study:
- To develop an efficient and sustainable catalytic strategy for synthesizing the isoindolinone (IIO) scaffold.
- To investigate the performance of a single-atom Pd/TiO2 tandem catalyst for IIO synthesis.
- To elucidate the mechanism of tandem catalysis involving TiO2 support and single-atom Pd.
Main Methods:
- Development of a single-atom palladium supported on titanium dioxide (Pd/TiO2) tandem catalyst.
- Utilized readily available starting materials: phthalic anhydride (PA), ammonia (NH3), and hydrogen (H2).
- Characterization of catalytic performance, including conversion, selectivity, and turnover frequency (TOF).
Main Results:
- Achieved high phthalic anhydride (PA) conversion (99%) and isoindolinone (IIO) selectivity (91%).
- Demonstrated a superior turnover frequency (TOF) of up to 4807 h⁻¹.
- Identified a tandem catalysis mechanism involving TiO2 and single-atom Pd, with NH3 acting as both reactant and promoter.
Conclusions:
- The single-atom Pd/TiO2 tandem catalyst provides an efficient and promising strategy for IIO scaffold synthesis.
- This catalytic system offers a sustainable alternative to conventional methods for producing key pharmaceutical intermediates.
- The synergistic effect between the TiO2 support and single-atom Pd is key to the catalyst's exceptional performance.
Related Concept Videos
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.0K
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.
10.0K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.2K
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...
3.2K
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
01:28Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
4.4K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
4.4K
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
7.7K
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.
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.
7.7K
01:16Cycloaddition Reactions: Overview
2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.5K