4.8 Article

Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 30, Pages 8772-8776

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503546

Keywords

aryldiazonium salt; cross-coupling; gold; redox catalysis

Funding

  1. NSF [CHE-1362057, CHE-1228336, CHE-1149367, CHE-1336071, EPS-1003907]
  2. NSFC [21228204]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1149367] Funding Source: National Science Foundation
  5. Direct For Mathematical & Physical Scien
  6. Division Of Chemistry [1619590] Funding Source: National Science Foundation

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Gold-catalyzed C(sp)-C(sp(2)) and C(sp(2))-C(sp(2)) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by Au-III reductive elimination as the key step.

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