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Kang, H. Ullmann Reaction. Encyclopedia. Available online: https://encyclopedia.pub/entry/60871 (accessed on 23 October 2026).
Kang H. Ullmann Reaction. Encyclopedia. Available at: https://encyclopedia.pub/entry/60871. Accessed October 23, 2026.
Kang, Helena. "Ullmann Reaction" Encyclopedia, https://encyclopedia.pub/entry/60871 (accessed October 23, 2026).
Kang, H. (2026, October 12). Ullmann Reaction. In Encyclopedia. https://encyclopedia.pub/entry/60871
Kang, Helena. "Ullmann Reaction." Encyclopedia. Web. 12 October, 2026.

Ullmann Reaction

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The Ullmann reaction is a copper-mediated coupling of aryl halides that forms a biaryl carbon–carbon bond. In its classical form, two aryl halide molecules are coupled by copper at elevated temperature, with loss of halide and creation of the bond between their ipso carbons [1]. Modern Ullmann-type chemistry extends the copper-mediated or copper-catalyzed manifold to arylation of nitrogen, oxygen, and sulfur nucleophiles, but these C–heteroatom variants are more precisely designated Ullmann-type amination, etherification, or thioetherification [2]. Proposed mechanisms depend on ligand, substrate, and conditions and can involve copper(I)/copper(III) cycles, single-electron pathways, or surface processes. The defining boundary of the original Ullmann reaction is reductive aryl–aryl coupling, which distinguishes it from nucleophilic aromatic substitution and from palladium-catalyzed cross-couplings. Both coupling partners are aryl fragments, and copper is the characteristic metal mediator.

Ullmann reaction copper coupling biaryl synthesis aryl halide
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References

  1. Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire; Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction. Chem. Rev. 2002, 102, 1359-1470. [CrossRef]
  2. Carlo Sambiagio; Stephen P. Marsden; A. John Blacker; Patrick C. McGowan; Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development. Chem. Soc. Rev. 2014, 43, 3525-3550. [CrossRef]
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Subjects: Chemistry, Organic
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register : Helena Kang
View Times: 2
Entry Collection: Organic Chemistry
Revision: 1 time (View History)
Update Date: 19 Oct 2026
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