Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions
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 <sup>31</sup>P NMR studies, mass analysis, and stoichiometric experiments, provided valuable insights into the reaction mechanism, which is further supported by computational studies.
Authors
- Nitin T. Patil (ORCID: https://orcid.org/0000-0002-8372-2759)
- Nivrutti B. Barhate
- Tanmayee Nanda (ORCID: https://orcid.org/0000-0001-6875-689X)
- Manoj V. Mane (ORCID: https://orcid.org/0000-0001-8236-3638)
- Prafulla Bera
Institutions
- Indian Institute of Science Education and Research, Bhopal (IN)
- Material Sciences (United States) (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-01
- DOI
- https://doi.org/10.1021/acs.orglett.5c01321
- Citations
- 5
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- Council of Scientific and Industrial Research, India
- Indian Institute of Science Education and Research Bhopal
- Science and Engineering Research Board