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<p>The arylation of olefines had a milestone year in 1939 when Hans Meerwein (1879–1965) reported that olefins could react with phenyldiazonium salts in the presence of a copper salt, facilitating the synthesis of various arylated products. Although widely applied in natural product and bioactive compound synthesis, the exact mechanism—whether it proceeds via phenyl cations or radicals—remains debated. This lecture text reviews the evolution of mechanistic insights, with recent studies highlighting the roles of substituents, solvent effects and radical intermediates, particularly in photoredox catalysis, as critical factors shaping reactivity and synthetic potential. These recent findings contribute to further advancements in organic synthesis.</p> Graphical Abstract: <p></p>

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Arylation of C=C bonds via non-cross-coupling reactions: historical evolution of the Meerwein arylation mechanisms

  • 期刊论文

  • 发表日期：

    2025年3月20日

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  • Leonardo S. A. Carneiro,
  • Camilla D. Buarque

摘要

The arylation of olefines had a milestone year in 1939 when Hans Meerwein (1879–1965) reported that olefins could react with phenyldiazonium salts in the presence of a copper salt, facilitating the synthesis of various arylated products. Although widely applied in natural product and bioactive compound synthesis, the exact mechanism—whether it proceeds via phenyl cations or radicals—remains debated. This lecture text reviews the evolution of mechanistic insights, with recent studies highlighting the roles of substituents, solvent effects and radical intermediates, particularly in photoredox catalysis, as critical factors shaping reactivity and synthetic potential. These recent findings contribute to further advancements in organic synthesis.

Graphical Abstract: