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Chemical Science
After a small modification of the reaction condition, several aryl halides and phenyl triflate were selectively
DOI: 10.1039/C9SC05532K
thiomethylated and gave the corresponding products in good to excellent yields. As shown in Fig. 4, good to excellent
yields of the desired aryl methyl sulfides can be obtained from the corresponding substrates bearing either electron-
deficient or electron-donating groups. ortho-Substituted aryl halides reacted well under our reaction conditions.
Heterocycles such as unprotected indole, benzothiazole and quinoline were well tolerated under our conditions. Notably,
4-bromophenylboronic acid, pinacol ester also reacted well in our reaction, which provides useful handles for further
synthetic transformations. Also the scope of thioesters, as shown in Fig 4, cyclohexanethio-, 1-decanethio- and arylthio-
can also be tolerated in our process and gave the desired products in good to excellent yields. After proving the
compatibility of aryl halides and thioesters of this methodology, we become interested in carbonylative thiomethylation.
Different aryl halides were tested under our standard conditions successively. The corresponding carbonylation products
were produced in good to excellent yields with excellent selectivity.
In conclusion, a novel palladium-catalyzed intermolecular transthioetherification reaction of aryl halides has been
developed. With alkyl sulfides, thioester and even nature products as a convenient functional reagent, different aryl
sulfides and thioester were obtained. Overall, the broad scope, excellent functional group compatibility, and high
efficiency allow for efficient and safe synthesis of related chemicals in pharmaceuticals and laboratory.
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Acknowledgements
The authors thank the financial supports from the National Key Research and Development Program of China
(2016YFD0200201), NSFC (21702197), Anhui Natural Science Foundation (19252004) and Anhui Leading Talent
Project (03011002).
Competing financial interests
The authors declare no competing financial interests.