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Synfacts 2013; 9(1): 0087
DOI: 10.1055/s-0032-1317733
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using S8/Organopolysulfides

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Arisawa M, * Ichikawa T, Yamaguchi M. * Tohoku University, Sendai, Japan
Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides.

Org. Lett. 2012;
14: 5318-5321
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

rhodium - sulfur - aryl fluorides - diaryl sulfides

Significance

The rhodium-catalyzed reaction of sulfur or organopolysulfides with aryl penta- and monofluorides in the presence of tributylsilane is disclosed. The corresponding diaryl sulfides are obtained in moderate to good yield.


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Comment

The mechanism is proposed to proceed via oxidative addition of the rhodium complex to the aryl fluoride and the SS–SS bond. After insertion of one sulfur atom, di-tert-butyl trisulfide is expelled and the rhodium–fluoride–aryl sulfide complex reacts with another aryl fluoride. The fluoride atoms are trapped with tributylsilane or triphenylphosphine and the corresponding diaryl sulfides are obtained after reductive elimination.


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