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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
5.2K
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

2.2K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
2.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.7K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.7K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

7.2K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
7.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

8.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
8.0K

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Transition Metals Catalyzed Element-Cyano Bonds Activations.

Rui Wang1, John R Falck2

  • 1Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, Dallas, Texas, USA ; Department of Chemistry, State University of New York at Albany, Albany, New York, USA.

Catalysis Reviews, Science and Engineering
|January 6, 2015
PubMed
Summary
This summary is machine-generated.

This review explores element-cyano bond cleavage reactions, crucial for organic synthesis. Transition metal catalysis enables efficient functionalization, creating new cyano groups and molecular skeletons in one pot.

Keywords:
Bond activationCarbon-carbon formationDehydrogenative coupling reactionsElements-cyanoTransition metals

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The cyano group is a vital intermediate in organic synthesis, readily converting to amines, amides, and acids.
  • Element-cyano bond cleavage offers a powerful strategy for one-pot synthesis of functionalized molecules.
  • Numerous element-cyano bonds (H-CN, Si-CN, C-CN, B-CN, Sn-CN, Ge-CN, S-CN, Halo-CN, N-CN, O-CN) are amenable to activation.

Purpose of the Study:

  • To review recent advancements in transition metal-catalyzed reactions involving element-cyano bond activation.
  • To highlight the versatility of cyano group transformations through bond cleavage strategies.
  • To provide a comprehensive summary of progress in this significant research area.

Main Methods:

  • Focus on transition metal catalysis for element-cyano bond activation.
  • Analysis of reactions involving cleavage of diverse element-cyano bonds.
  • Literature review of synthetic methodologies and applications.

Main Results:

  • Demonstration of efficient cyano group introduction and skeleton functionalization via element-cyano bond cleavage.
  • Highlighting the broad scope of applicable element-cyano bonds.
  • Showcasing the utility of transition metal catalysts in these transformations.

Conclusions:

  • Element-cyano bond activation is a key strategy for accessing diverse functionalized molecules.
  • Transition metal catalysis plays a pivotal role in enabling these transformations.
  • This methodology offers significant potential for streamlined organic synthesis.