Synthesis 2017; 49(22): 5025-5038
DOI: 10.1055/s-0036-1588508
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed C–S Bond Formation via the Cleavage of C–O Bonds in the Presence of S8 as the Sulfur Source

Abed Rostamia, Amin Rostami*a, Arash Ghaderi*b, Mohammad Gholinejadc, Sajedeh Gheisarzadeha
  • aDepartment of Chemistry, Faculty of Science, University of Kurdistan, 66177-15175 Sanandaj, Iran   Email: a_rostami372@yahoo.com
  • bDepartment of Chemistry, College of Sciences, Hormozgan University, 71961 Bandar Abbas, Iran   Email: aghaderi@hormozgan.ac.ir
  • cDepartment of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, 5137-66731 Zanjan, Iran
Further Information

Publication History

Received: 21 June 2017

Accepted after revision: 23 June 2017

Publication Date:
03 August 2017 (eFirst)

Abstract

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.

Supporting Information

 
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