Metal–organic framework MOF-199-catalyzed direct and one-pot synthesis of thiols, sulfides and disulfides from aryl halides in wet polyethylene glycols (PEG 400)

ABSTRACT

A highly porous metal–organic frame work Cu₃ BTC₂ (copper(II)-benzene-1,3,5-tricarboxylate) that is known as MOF-199 was synthesized from the reaction of 1,3,5-benzenetricarboxylic acid and Cu(OAc)₂·H₂O by a solvothermal method and characterized by several techniques including FT-IR, XRD, EDX and scanning electron microscopy. The MOF-199 used as an efficient catalyst for one-pot synthesis of thiols by domino reactions of aryl halides and thiourea, and subsequently conversion to aryl alkyl sulfides and diaryl disulfides in polyethylene glycols (PEGs). A variety of aryl alkyl sulfides can be obtained in good to excellent yields in a relatively short reaction time and in the presence of the trace amount of catalyst. Also, the catalyst can be separated from the reaction mixture by decanting, and be reused without significant degradation in catalytic activity.

GRAPHICAL ABSTRACT

KEYWORDS:

• Metal–organic framework
• 1,3,5-benzenetricarboxylic acid
• Cu(OAc)₂·H₂O
• aryl alkyl sulfides
• polyethylene glycols

Disclosure Statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the Ilam University Research Council.