Related Experiment Video
Updated: Jan 2, 2026
07:06
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
8.5K
Pd and Mo Catalyzed Asymmetric Allylic Alkylation
1Department of Chemistry, Stanford University, Stanford, CA 94305-5080.
Organic Process Research & Development
|June 28, 2012
Summary
Metal catalysts enable powerful asymmetric alkylation of organic molecules. This review details palladium and molybdenum catalysts for synthesizing bioactive compounds by forming diverse chemical bonds.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- Metal catalysis significantly enhances control over organic substrate alkylation.
- Asymmetric catalysis offers efficient stereoinduction using chiral ligands with metals.
- A single catalyst system can facilitate asymmetric formation of various bonds (C-C, C-N, C-O, C-S, C-P, C-H).
Purpose of the Study:
- To provide an overview of asymmetric metal-catalyzed alkylation processes.
- To highlight the development of palladium and molybdenum-based catalysts.
- To discuss the strategic application of these catalysts in synthesizing bioactive molecules.
Main Methods:
- Development of novel palladium and molybdenum catalyst systems.
- Investigation of asymmetric bond-forming reactions.
- Application in the synthesis of complex molecular targets.
Main Results:
- Demonstration of versatile asymmetric bond formation (C-C, C-N, C-O, C-S, C-P, C-H) using metal catalysts.
- Successful application of developed catalysts in synthesizing bioactive molecules.
- Insights into stereochemical control mechanisms in metal-catalyzed reactions.
Conclusions:
- Asymmetric metal catalysis provides powerful tools for organic synthesis.
- Palladium and molybdenum catalysts offer strategic advantages for creating complex bioactive molecules.
- The development of efficient catalytic systems is crucial for advancing synthetic chemistry.
Related Concept Videos
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.8K
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...
3.8K
01:25Radical Anti-Markovnikov Addition to Alkenes: Overview
3.9K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.9K
01:10α-Alkylation of Ketones via Enolate Ions
3.7K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.7K
01:27Radical Substitution: Allylic Bromination
6.4K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.4K
02:35Regioselectivity of Electrophilic Additions-Peroxide Effect
10.1K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.1K
01:22Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
2.2K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.2K