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Title
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Copper-Catalyzed C–S Bond Formation via the Cleavage of C–O Bonds in the Presence of S8 as the Sulfur Source
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Type
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JournalPaper
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Keywords
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phenolic esters, arylboronic acid, triphenyltin chloride, copper salt, catalyst, sulfides
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Abstract
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Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C–O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S8/KF or S8/NaOt-Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S8 as the sulfur source and NaOt-Bu in anhydrous DMF at 120 °C under N2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
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Researchers
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ghaysarzadeh SAJEDEH (Fifth Researcher), Mohammad Gholinejad (Fourth Researcher), Arash Ghaderi (Third Researcher), Amin Rostami (Second Researcher), Abed Rostami (First Researcher)
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