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Related Concept Videos

Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

5.4K
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.
5.4K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

11.0K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
11.0K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.1K
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

2.0K
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.
2.0K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

1.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
1.3K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
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.
2.4K

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Reductive cross-coupling reactions between two electrophiles.

Christiane E I Knappke1, Sabine Grupe, Dominik Gärtner

  • 1Chemistry Research Laboratory, University of Oxford (U.K.).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 15, 2014
PubMed
Summary

Reductive cross-electrophile coupling offers a sustainable method for C-C bond formation using inexpensive electrophiles and metal catalysts. This approach avoids hazardous organometallic reagents, simplifying synthetic procedures.

Keywords:
biarylscross-couplingmetalationreductionsustainable chemistry

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Reductive cross-electrophile coupling reactions have emerged as powerful tools for C-C bond formation.
  • These methods offer a sustainable alternative by utilizing readily available and inexpensive electrophiles.
  • They circumvent the need for pre-formed and potentially hazardous organometallic reagents.

Purpose of the Study:

  • To provide a comprehensive overview of recent advancements in reductive cross-electrophile coupling.
  • To summarize key protocols involving diverse electrophile combinations (alkyl, alkenyl, allyl, aryl).
  • To highlight significant mechanistic investigations in the field.

Main Methods:

  • In situ reductive coupling reactions.
  • Utilizing transition-metal catalysts such as Nickel (Ni), Cobalt (Co), Palladium (Pd), and Iron (Fe).
  • Employing metallic reductants including Manganese (Mn), Zinc (Zn), and Magnesium (Mg).

Main Results:

  • Demonstrated versatility in forming C-C bonds with various organic fragments.
  • Successful implementation of reactions using earth-abundant metals as catalysts and reductants.
  • Provided insights into the mechanistic pathways governing these coupling reactions.

Conclusions:

  • Reductive cross-electrophile coupling represents a versatile and sustainable synthetic strategy.
  • The methodology enables selective C-C bond formation with improved safety and cost-effectiveness.
  • Ongoing mechanistic studies continue to refine and expand the scope of these important reactions.