Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides

Arisawa, Mieko; Ichikawa, Takuya; Yamaguchi, Masahiko

doi:10.1021/ol302497m

Cited by 58 publications

(18 citation statements)

References 32 publications

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“…The [RhH(PPh 3 ) 4 ]‐catalyzed synthesis of bis(4‐substituted 2,3,5,6‐tetrafluorophenyl) sulfides by using substituted pentafluorobenzenes and S 8 was developed by Arisawa, Yamaguchi, and co‐workers through C(sp 2 )F bond activation (Scheme ) 14…”

Section: Cs Bond Construction By Different Sulfuration Agentsmentioning

confidence: 99%

Transfer of Sulfur: From Simple to Diverse

Liu

Jiang

2013

Chemistry An Asian Journal

565

146

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The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration agents have been developed for thionation reactions over the past few decades. In this Focus Review, we collect and summarize the C-S bond-formation reactions that have been used to construct C-S bonds in natural products and pharmaceutical compounds.

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Section: Cs Bond Construction By Different Sulfuration Agentsmentioning

confidence: 99%

Transfer of Sulfur: From Simple to Diverse

Liu

Jiang

2013

Chemistry An Asian Journal

565

146

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“…The phenomenon was ascribed to the slow formation of active sulfur species because preheating sulfur in acetone for 1.5 h eliminated the induction period. Symmetric diaryl sulfides are synthesized from perfluorobenzene and sulfur involving C-F bond activation, which showed reactivity and the p-difluoride rule similar to disulfides (Scheme 26) [63]. Treatment of 4-phenylthiopentafluorobenzene, sulfur, and tributylsilane in DMF at room temperature in the presence of RhH(PPh 3 ) 4 (5 mol%) and dppBz (10 mol%) provided bis(4-cyano-2,3-5,6-tetrafluorophenyl) sulfides in 77% yield.…”

Section: Rhodium-catalyzed Reactions Of Sulfurmentioning

confidence: 99%

Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur

Arisawa

Yamaguchi

2020

Molecules

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Organosulfur compounds are widely used for the manufacture of drugs and materials, and their synthesis in general conventionally employs nucleophilic substitution reactions of thiolate anions formed from thiols and bases. To synthesize advanced functional organosulfur compounds, development of novel synthetic methods is an important task. We have been studying the synthesis of organosulfur compounds by transition-metal catalysis using disulfides and sulfur, which are easier to handle and less odiferous than thiols. In this article, we describe our development that rhodium complexes efficiently catalyze the cleavage of S-S bonds and transfer organothio groups to organic compounds, which provide diverse organosulfur compounds. The synthesis does not require use of bases or organometallic reagents; furthermore, it is reversible, involving chemical equilibria and interconversion reactions.

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“…Substituted pentafluorobenzenes 213 reacted with elemental sulfur to provide bis(2,3,5,6‐tetrafluorophenyl) sulfides 214 in the presence of catalytic amounts of the RhH(PPh 3 ) 4 complex and 1,2‐bis(diphenylphosphino)benzene (dppBz) ligand (Scheme ) …”

Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides

Cited by 58 publications

References 32 publications

Transfer of Sulfur: From Simple to Diverse

Transfer of Sulfur: From Simple to Diverse

Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur

Recent Advances in Organic Reactions Involving Elemental Sulfur

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