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Updated: May 12, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Gold-Catalyzed Deallylative C-S Cross-Coupling Reactions
Prafulla Bera1, Tanmayee Nanda1, Nayan A Barhate1
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri 462 066, India.
Abstract:
Herein, we report the gold-catalyzed deallylative C-S cross-coupling reaction through ligand-enabled Au(I)/Au(III) redox catalysis. One of the major challenges in gold-catalyzed C-S cross-coupling reactions is to prevent catalyst deactivation caused by the formation of a strong gold-sulfur bond. We discovered that the use of allyl phenyl sulfide as a sulfur surrogate facilitates a dynamic equilibrium between cationic Au(I) and Au(I)-sulfide complexes, overcoming the gold quenching problem. A detailed mechanistic investigation, including 31P NMR studies, mass analysis, and stoichiometric experiments, provided valuable insights into the reaction mechanism, which is further supported by computational studies.
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