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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...

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This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

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Published on: January 4, 2018

Switchable aqueous catalytic systems for organic transformations.

Nikita Das¹, Chandan Maity²

¹Department of Chemistry, School of Advanced Sciences (SAS), Vellore Institute of Technology (VIT), Vellore, 632014, Tamil Nadu, India.

Communications Chemistry

|January 25, 2023

Summary

This summary is machine-generated.

Researchers review switchable catalytic systems that mimic enzymes. These smart catalysts offer controlled reactions in aqueous environments, paving the way for advanced biomaterials and chemical biology applications.

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Area of Science:

Biomimetic chemistry
Catalysis
Materials science

Background:

Enzyme catalysis in organisms offers precise control in aqueous media.
Biomimetic artificial catalysts are inspired by enzymes but struggle in aqueous environments.
Controlling reaction rate and selectivity is key for smart catalytic systems.

Purpose of the Study:

To summarize stimuli-responsive catalytic systems with switchable activity in aqueous environments.
To classify these systems based on the type of stimulus used.
To highlight their potential in biomedicine and chemical biology.

Main Methods:

Review of existing literature on switchable catalytic systems.
Classification of systems by stimulating agent (e.g., light, pH, temperature).
Discussion of organic transformations enabled by these catalysts.

Main Results:

Identification of various stimuli-responsive catalytic systems.
Demonstration of 'on'/'off' switching of catalytic activity.
Examples of organic transformations performed in aqueous media.

Conclusions:

Switchable catalytic systems offer precise control in aqueous environments, mimicking natural enzymes.
These systems hold significant promise for developing smart materials in biomedicine and chemical biology.
Further engineering of aqueous catalytic systems is expected to expand their applications.