Journal Article10.1021/JA0580340
A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.
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TL;DR: A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand and the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.
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Abstract: A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.
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Citations
Recent applications of chiral ferrocene ligands in asymmetric catalysis.
TL;DR: This Review documents recent advances in asymmetric catalysis, with special emphasis on the most innovative asymmetric processes and the development of novel, efficient types of ferrocene ligands.
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Cobalt-Catalyzed Cross-Coupling Reactions
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Activation of “Inert” Alkenyl/Aryl C ? O Bond and Its Application in Cross‐Coupling Reactions
TL;DR: This review summarizes the transition-metal-catalyzed cross-coupling of enol- and phenol-based electrophiles, including phosphates, sulfonates, ethers, carboxylates, and Phenolates.
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Transition-metal-catalyzed C-S bond coupling reaction.
TL;DR: Recent efforts in metal-catalyzed C-S bond cross-coupling reactions are summarized, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.
429
References
Handbook of organopalladium chemistry for organic synthesis
Ei-ichi Negishi
- 26 Jul 2002
TL;DR: Palladium-CATALYZED Reactions Involving Nucleophilic Attack on -Ligands of Palladium-Alkene, PalladiumAlkyne, and Related Derivatives as mentioned in this paper.
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A General Palladium-Catalyzed Coupling of Aryl Bromides/Triflates and Thiols
Takahiro Itoh,Toshiaki Mase +1 more
TL;DR: An efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryL chloride is developed that has shown tolerance to a wide variety of aries and alkyl thiols that can also be used as sulfide equivalents.
480
Modern Arene Chemistry
Didier Astruc
- 01 Oct 2002
TL;DR: The state-of-the-art arene chemistry can be found in this article, where the authors discuss the development of the Suzuki reaction with Arylboron compounds in arene Chemistry.
462
A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines
Miki Murata,Stephen L. Buchwald +1 more
TL;DR: In this paper, a broad substrate scope of aryl bromides and chlorides can be coupled to aliphatic and aromatic thiols using Pd(OAc)2/1, 1,1,1′-bis(diisopropylphosphino)ferrocene as the catalyst.
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