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Rhodium-catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and sulfur/organopolysulfides

Rhodium-catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and sulfur/organopolysulfides

Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi

Org Lett. 2012 Oct 19;14(20):5318-21.

PMID: 23039101

Abstract:

Substituted pentafluorobenzenes react with sulfur to give bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides in the presence of RhH(PPh(3))(4), 1,2-bis(diphenylphosphino)benzene (dppBz), and tributylsilane. The reaction proceeds efficiently between room temperature and 80 °C. A comparative study of the reactivities of an organic trisulfide and a tetrasulfide showed notable substrate specificity. Di-tert-butyl tetrasulfide reacted with reactive aryl monofluorides and substituted pentafluorobenzenes. Di-tert-butyl trisulfide reacted with aryl monofluorides. The reactivity was explained on the basis of the difference in S-S bond energy.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18765098	Trioctylsilane		18765-09-8	Price

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