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Related Concept Videos

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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.
Cycloaddition Reactions: Overview01:16

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.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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.
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

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Related Experiment Video

Updated: May 31, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Silicon-based cross-coupling reaction: an environmentally benign version.

Yoshiaki Nakao1, Tamejiro Hiyama

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. yoshiakinakao@npc05.mbox.media.kyoto-u.ac.jp

Chemical Society Reviews
|July 15, 2011
PubMed
Summary
This summary is machine-generated.

Silicon-based cross-coupling reactions offer a stable and non-toxic alternative for chemical synthesis. Recent advances focus on designing organosilicon reagents that efficiently undergo transmetalation for diverse coupling applications.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry

Background:

  • Organosilicon compounds are increasingly utilized in cross-coupling reactions due to silicon's stability, non-toxicity, and abundance.
  • Silicon-based cross-coupling offers advantages over traditional methods, driving research into novel synthetic protocols.

Purpose of the Study:

  • To review successful examples of silicon-based cross-coupling reactions, emphasizing advancements in the last decade.
  • To highlight the critical role of organosilicon reagent design in facilitating transmetalation, a key step in these reactions.

Main Methods:

  • Classification of organosilicon reagents based on silicon substituents.
  • Survey of cross-coupling reactions involving various organosilicon reagents and electrophiles.

Main Results:

  • Demonstration of effective palladium catalysts, often adapted from other coupling reactions, for silicon-based protocols.
  • Identification of specific organosilicon reagent structures that promote efficient transmetalation.
  • Compilation of diverse cross-coupling examples utilizing these reagents.

Conclusions:

  • The development of silicon-based cross-coupling is significantly advanced by tailored organosilicon reagent design.
  • These methods provide a versatile and sustainable approach to forming carbon-carbon and carbon-heteroatom bonds.