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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Elimination Reactions02:25

Elimination Reactions

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 β elimination or...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only in the...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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...
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...

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Related Experiment Video

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

A remote Lewis acid trigger dramatically accelerates biaryl reductive elimination from a platinum complex.

Allegra L Liberman-Martin1, Robert G Bergman, T Don Tilley

  • 1Department of Chemistry, University of California - Berkeley, Berkeley, California 94720, USA.

Journal of the American Chemical Society
|June 25, 2013
PubMed
Summary

This study introduces a novel method to control electron density at metal centers using a remote chemical switch. This approach significantly accelerates a key chemical reaction, biaryl reductive elimination, by over 64,000 times.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Catalysis

Background:

  • Controlling electron density at metal centers is crucial for tuning reactivity.
  • Second-sphere interactions offer a pathway to influence the first coordination sphere.
  • Platinum(II) complexes are important in catalysis and materials science.

Purpose of the Study:

  • To develop a strategy for remote electronic control of metal centers.
  • To investigate the effect of Lewis acid binding on platinum complex reactivity.
  • To enhance the rate of biaryl reductive elimination.

Main Methods:

  • Synthesis of a bipyrazine-diarylplatinum(II) complex.
  • Utilizing a remote chemical switch involving Lewis acid binding (B(C6F5)3).
  • Kinetic studies to measure reaction rates.

Main Results:

  • Demonstrated successful modulation of electron density via second-sphere Lewis acid binding.
  • Observed a significant acceleration of biaryl reductive elimination by a factor of 64,000.
  • Established a robust method for controlling metal center reactivity.

Conclusions:

  • Remote Lewis acid binding is an effective strategy for electronic control of metal centers.
  • This method provides unprecedented control over reaction rates in organometallic complexes.
  • The findings have implications for catalyst design and development.