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Related Concept Videos

Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.8K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.8K
Elimination Reactions02:25

Elimination Reactions

17.9K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
17.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.7K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.7K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

4.2K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
4.2K
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

4.5K
Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
4.5K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

4.1K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
4.1K

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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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Carbon-Fluorine Reductive Elimination from Nickel(III) Complexes.

Heejun Lee1,2, Jonas Börgel1, Tobias Ritter1,2

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

Angewandte Chemie (International Ed. in English)
|May 12, 2017
PubMed
Summary

Researchers achieved a C-F reductive elimination from a nickel(III) complex. This reaction is faster than any previously observed C-F bond formation in similar metal fluoride compounds.

Keywords:
aryl fluoridesfluorinationnickelreductive elimination

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry

Background:

  • C-F bond activation is crucial for synthetic chemistry.
  • Aryl metal fluoride complexes are key intermediates.
  • Reductive elimination is a vital step in catalytic cycles.

Purpose of the Study:

  • To report the first C-F reductive elimination from a characterized first-row aryl metal fluoride complex.
  • To investigate the kinetics of C-F reductive elimination in nickel(III) complexes.

Main Methods:

  • Synthesis and characterization of a nickel(III) aryl metal fluoride complex.
  • Kinetic studies to determine reaction rates of C-F reductive elimination.

Main Results:

  • Successful C-F reductive elimination was observed from the nickel(III) complex.
  • The rate of reductive elimination was found to be significantly faster than previously reported for similar complexes.

Conclusions:

  • First-row transition metal complexes can undergo C-F reductive elimination.
  • Nickel(III) complexes offer a promising platform for efficient C-F bond activation.