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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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 reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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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.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Ambiphilic cross-coupling with aryl-bismuth reagents.

Byeongdo Roh1, Benedict A Williams1, Josep Cornella2

  • 1Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.

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|April 9, 2026
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Summary

Researchers developed ambiphilic aryl-bismuth reagents for transition metal-catalyzed cross-coupling reactions. These reagents can act as both nucleophiles and electrophiles, challenging traditional mechanistic assumptions in aryl-aryl bond formation.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Cross-coupling reactions form aryl-aryl bonds using transition metal catalysis.
  • Reactivity relies on distinct nucleophilic and electrophilic aryl partners.
  • Mechanistic roles are typically dictated by intrinsic bond polarity.

Purpose of the Study:

  • To introduce ambiphilic aryl-bismuth reagents.
  • To demonstrate their dual nucleophilic and electrophilic reactivity in cross-coupling.
  • To challenge established mechanistic paradigms in cross-coupling chemistry.

Main Methods:

  • Synthesis of novel aryl-bismuth compounds.
  • Investigation of their reactivity in transition metal-catalyzed cross-coupling reactions.
  • Stoichiometric and mechanistic studies to elucidate reaction pathways.

Main Results:

  • Demonstrated that aryl-bismuth reagents can act as both nucleophiles and electrophiles.
  • Showcased their ability to undergo both oxidative addition and transmetalation.
  • Established a new class of ambiphilic reagents for cross-coupling.

Conclusions:

  • Aryl-bismuth reagents break the traditional dichotomy of nucleophilic/electrophilic roles.
  • This ambiphilic reactivity challenges the assumption that bond polarity dictates mechanistic function.
  • Opens new avenues for designing cross-coupling reactions with unprecedented flexibility.