25752-91-4Relevant articles and documents
Transalkylation of alkyl aryl sulfides with alkylating agents
Nawrot, Daria,Koleni?, Marek,Kune?, Ji?í,Kostelansky, Filip,Miletin, Miroslav,Novakova, Veronika,Zimcik, Petr
, p. 594 - 599 (2018/01/01)
The reaction of methyl iodide with tert-butylphenylsulfide in DMF leads to a transalkylation that produces methylphenylsulfide. This transalkylation reaction was further studied by 1H NMR spectroscopy. The polarity of the solvent, the electron density on the sulfur atom, and the strength of the alkylating agent (MeI, EtI, BuI, dimethyl sulfate, or dimethyl carbonate) played important roles in the reaction. The suggested mechanism of the reaction involves the formation of a dialkyl aryl sulfonium salt that subsequently eliminates the radical. This mechanism was supported by the observation of higher conversion rates for compounds with more branched alkyl groups on the sulfur atom, which may lead to the formation of more stable radicals.
A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides
Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
experimental part, p. 1664 - 1672 (2009/07/17)
The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols
Fernandez-Rodriguez, Manuel A.,Shen, Qilong,Hartwig, John F.
, p. 2180 - 2181 (2007/10/03)
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. Copyright
