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.

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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

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article

Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions

Nitin T. Patil, Nivrutti B. Barhate, Tanmayee Nanda, Manoj V. Mane et al.
5 citations
Organic Letters
Sulfur-Based Synthesis Techniques
4.68
article

Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions

Nitin T. Patil, Nivrutti B. Barhate, Tanmayee Nanda, Manoj V. Mane, Prafulla Bera
article en
5 citations

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 <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.

Organic LettersVol. 27(18)
Indian Institute of Science Education and Research, Bhopal (IN), Material Sciences (United States) (US)
Council of Scientific and Industrial Research, India, Indian Institute of Science Education and Research Bhopal, Science and Engineering Research Board
Openalex Percentile: Top 6%
Sulfur-Based Synthesis Techniques
4.68
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