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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

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.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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.

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Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function

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Programmed alternating current optimization of Cu-catalyzed C-H bond transformations.

Li Zeng¹, Qinghong Yang¹, Jianxing Wang¹

¹Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China.

Science (New York, N.Y.)

|July 11, 2024

Summary

This summary is machine-generated.

Programmed alternating current (pAC) electrosynthesis offers a new method for chemical synthesis. This technique improves copper-catalyzed reactions, outperforming direct current methods and providing mechanistic insights.

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Area of Science:

Electrochemistry
Organic Synthesis
Catalysis

Background:

Direct current (DC) electrosynthesis is well-established in industry.
Alternating current (AC) electrosynthesis has potential but lacks development in apparatus, principles, and applications.

Purpose of the Study:

Introduce a protocol for programmed AC (pAC) electrosynthesis.
Explore the application of pAC in copper-catalyzed reactions.
Gain mechanistic insight into catalyst behavior under varying waveforms.

Main Methods:

Developed a protocol for programmed AC (pAC) electrosynthesis with adjustable currents, frequencies, and duty ratios.
Applied representative pAC waveforms to copper-catalyzed C-H bond cleavage reactions.
Investigated catalyst dynamics under different waveform conditions.

Main Results:

pAC electrosynthesis facilitated copper-catalyzed C-H bond cleavage in cross-coupling and difunctionalization reactions.
Achieved superior performance compared to DC electrosynthesis and chemical oxidation.
Observed dynamic catalyst variations providing mechanistic understanding.

Conclusions:

Programmed AC electrosynthesis is a versatile tool for challenging organic transformations.
pAC offers advantages over traditional DC methods for specific catalytic reactions.
The study provides valuable mechanistic insights into electrocatalysis through waveform control.