Ppm level palladium catalyzed regioselective remote arylation of alkenyl alcohols
View abstract on PubMed
Summary
This summary is machine-generated.This study introduces a highly efficient palladium-catalyzed reaction using parts per million (ppm) palladium concentrations for remote arylation of alkenols. This method offers cost-effective and scalable solutions for pharmaceutical manufacturing.
Area Of Science
- Organic Chemistry
- Catalysis
- Green Chemistry
Background
- Palladium catalysis is crucial in chemical synthesis.
- Minimizing palladium catalyst loading is essential for cost reduction and sustainability.
- Low palladium concentrations reduce purification challenges and metal contamination in products.
Purpose Of The Study
- To develop a parts per million (ppm) level palladium-catalyzed remote arylation of alkenols.
- To achieve high efficiency, regioselectivity, and versatility in carbonyl scaffold construction.
- To demonstrate the applicability of this method for pharmaceutical and fine chemical manufacturing.
Main Methods
- Utilized ppm level palladium catalyst for remote arylation.
- Employed alkenols as substrates for the reaction.
- Optimized reaction conditions for efficiency and selectivity.
Main Results
- Achieved high efficiency and regioselectivity in the remote arylation of alkenols.
- Demonstrated flexible construction of carbonyl scaffolds.
- Showcased excellent compatibility with styrene-derived substrates.
- Successfully scaled the reaction to gram quantities.
Conclusions
- Developed a cost-effective and sustainable method for remote arylation using low palladium concentrations.
- The strategy provides a robust foundation for large-scale applications in pharmaceutical and fine chemical industries.
- Highlights the potential of ppm-level palladium catalysis in modern synthesis.
Related Concept Videos
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
The observed regioselectivity can be explained based on the radical stability and steric effect. From the radical stability perspective, adding hydrogen bromide in the presence of peroxide directs the bromine radical at the less substituted carbon via a more stable tertiary radical intermediate. Similarly, in the steric framework, the...
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.
In the first...
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Mechanism
The hydroboration-oxidation reaction is a two-step...
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
Phosphorus ylide is a neutral molecule containing a negatively charged carbon directly bonded to a positively charged phosphorus atom. The molecule is stabilized by resonance.
The Wittig reagents are synthesized from unhindered alkyl halides in two...
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
The reaction takes place in two steps:
1. The first step is the deprotonation of the terminal alkyne by the strong base forming an acetylide ion.
2. The second step is a nucleophilic...

