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Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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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...
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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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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...
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Cobalt-Catalyzed Reductive Cross-Coupling Between Styryl and Benzyl Halides.

Yingxiao Cai1, Andreas D Benischke2, Paul Knochel2

  • 1LCM, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 21, 2016
PubMed
Summary

A new cobalt-manganese catalyzed cross-coupling reaction efficiently joins alkenyl and benzyl halides. This method tolerates various functional groups, offering a versatile approach for synthesizing complex organic molecules.

Keywords:
alkenylbenzylcobaltcross-couplingretention of configuration

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Direct reductive cross-coupling reactions are crucial for C-C bond formation in organic synthesis.
  • Developing efficient and selective catalytic systems for coupling alkyl halides with alkenyl halides remains a significant challenge.
  • Transition-metal catalysis offers powerful tools for constructing complex molecular architectures.

Purpose of the Study:

  • To develop a simple and efficient protocol for the direct reductive cross-coupling between alkenyl and benzyl halides.
  • To explore the scope and limitations of a novel Co/Mn catalytic system for this transformation.
  • To investigate the mechanistic pathway and stereospecificity of the developed reaction.

Main Methods:

  • Utilized a [CoBr2(PPh3)2] catalyst with NaI as an additive in acetonitrile.
  • Investigated the reaction with a broad range of functionalized alkenyl and benzyl halides.
  • Employed mechanistic studies to propose a radical chain mechanism.

Main Results:

  • Achieved direct reductive cross-coupling between alkenyl and benzyl halides with a Co/Mn system.
  • Demonstrated tolerance of diverse functional groups on both coupling partners.
  • Obtained moderate to excellent yields, showcasing the reaction's efficiency and broad scope.

Conclusions:

  • A novel and efficient Co/Mn-catalyzed protocol for direct reductive cross-coupling of alkenyl and benzyl halides has been established.
  • The reaction exhibits broad substrate scope and functional group tolerance, significantly advancing transition-metal-catalyzed benzylation of alkenyl halides.
  • The proposed radical chain mechanism and observed stereospecificity provide valuable insights into the reaction's behavior.