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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.

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

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...

Phase I Reactions: Reductive Reactions

Phase I Reactions: Reductive Reactions

Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.

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...

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The Progress of Reductive Coupling Reaction by Iron Catalysis.

Jian-Qiang Zhao¹, Zhang-Pei Chen²

¹Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, 610106, China.

Chemical Record (New York, N.Y.)

|September 18, 2024

Summary

Iron-catalyzed reductive coupling reactions offer an efficient and sustainable method for forming carbon-carbon bonds. This approach avoids sensitive reagents and provides unique advantages in organic synthesis.

Keywords:

C−C bonding formation iron catalysis organic synthesis radical reaction reducing coupling

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Transition metal-catalyzed coupling reactions are crucial for C-C bond formation.
Reductive coupling offers advantages over traditional cross-coupling by avoiding sensitive organometallic reagents.
Iron catalysis is gaining attention due to its cost-effectiveness and environmental benefits.

Purpose of the Study:

To provide an overview of recent advances in iron-catalyzed reductive coupling reactions.
To discuss the mechanisms of these reactions.
To highlight the utility of iron in C-C bond formation.

Main Methods:

Review of recent literature on iron-catalyzed reductive coupling.
Analysis of reaction mechanisms.
Discussion of advantages and applications in organic synthesis.

Main Results:

Iron-catalyzed reductive coupling reactions are increasingly popular due to their efficiency and sustainability.
These reactions offer good step economy and functional group tolerance.
Iron catalysis provides an orthogonal approach to classical coupling methods.

Conclusions:

Iron-catalyzed reductive coupling reactions represent a significant advancement in C-C bond formation.
They offer a greener and more accessible alternative to traditional methods.
Further exploration of iron catalysis in synthesis is warranted.