Nickel-Catalyzed Synthesis of Aryl Trifluoromethyl Sulfides at Room Temperature

Zhang, Cheng‐Pan; Vicic, David A.

doi:10.1021/ja210364r

Cited by 330 publications

(96 citation statements)

References 12 publications

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“…Adachi’s group started a search for efficient TADF materials from tin (IV) fluoride-porphyrin complexes. TADF materials with various colors were reported [53, 54], and remarkable materials of pure blue with 10% EQE [55], deep blue with 14.5% EQE [56] and very high EQE of 16.5% [57] were obtained. This material design is expected to be introduced into polymer OLED materials.…”

Section: Polymer Oledmentioning

confidence: 99%

Recent progress of high performance polymer OLED and OPV materials for organic printed electronics

Sekine

Tsubata

Yamada

et al. 2014

Science and Technology of Advanced Materials

292

202

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The development of organic printed electronics has been expanding to a variety of applications and is expected to bring innovations to our future life. Along with this trend, high performance organic materials with cost-efficient fabrication processes and specific features such as thin, light weight, bendable, and low power consumption are required. A variety of organic materials have been investigated in the development of this field. The basic guidelines for material design and the recent progress of polymer-based organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs) are reported.

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Section: Polymer Oledmentioning

confidence: 99%

Recent progress of high performance polymer OLED and OPV materials for organic printed electronics

Sekine

Tsubata

Yamada

et al. 2014

Science and Technology of Advanced Materials

292

202

View full text Add to dashboard Cite

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“…Some nucleophilic reactions have previously been realized through the use of stabilized forms of the unstable CF 3 S anion, but apart from CF 3 SCu the reactivity of these species is relatively limited; [10] such reagents are generally not stable enough to be stored for extended periods. Most recently, metal-catalyzed coupling reactions with CF 3 SAg [11] or CF 3 SNMe 4 [12] have been described. However, the reagents are not very stable and must be prepared before use.…”

mentioning

confidence: 99%

“…[13] Nevertheless, these recent direct trifluoromethanesulfanylations are essentially limited to aromatic compounds. Furthermore, whereas researchers have shown renewed interest in nucleophilic strategies, [11][12][13] electrophilic methods remain underdeveloped.…”

mentioning

confidence: 99%

Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides

2012

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“…The antiparasitic drug Toltrazuril and insecticide Fipronil are two successful examples of this class of compounds. [4][5][6][7] Lipophilicity is often crucial for drug uptake and intracellular accumulation and can therefore decide on the bioactivity of a drug molecule. 3 An impressive number of procedures and reagents have been recently reported to introduce an S-CF 3 group into various molecules.…”

Section: Introductionmentioning

confidence: 99%

“…3 An impressive number of procedures and reagents have been recently reported to introduce an S-CF 3 group into various molecules. 4,[7][8][9] However, the currently available publications in this field are mainly focusing on purely organic compounds. The number of reports describing the preparation of S-CF 3 -containing and more generally of fluorine-containing organometallic complexes is indeed relatively scarce.…”

Section: Introductionmentioning

confidence: 99%

Novel, Mercury-Free Synthetic Pathway for Trifluoromethylthio-Substituted Metallocenes

et al. 2014

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A novel synthetic pathway for trifluoromethylthioferrocene (3), which does not involve the use of toxic mercury(II)-based reagents, is described. The novel approach involves first the treatment of the commercially available bromoferrocene (1a) with NaSCN in the presence of copper(+I) to yield thiocyanatoferrocene (1), and then the reaction of 1 with the Rupper-Prakash reagent and tetrabutylammonium fluoride (TBAF) to give 3 in an overall yield of 60%. This approach could be extended for the preparation of thiocyanato-(4) and trifluoromethylthio-ruthenocene (7), which are herein both reported for the first time. Interestingly, diferrocenyl disulfide (2a) and diruthenocenyl disulfide (5) could be isolated as side-products during the synthesis of 3 and 7, respectively. All new compounds were unambiguously characterized by (1)H, (13)C, and (19)F NMR spectroscopy, mass spectrometry, cyclic voltammetry, elemental analysis, as well by X-ray crystallography for 1, 4, 4b, 5, 6, and 7. 1-7 were further tested for their toxic activity on cervical cancer (HeLa) and noncancerous (MRC-5) cell lines. All organometallic compounds were found either to be nontoxic or to have a moderate toxicity toward the cell lines used in this study. ABSTRACT: A novel synthetic pathway for trifluoromethylthioferrocene (3), which does not involve the use of toxic mercury(II)-based reagents, is described. The novel approach involves first the treatment of the commercially available bromoferrocene (1a) with NaSCN in the presence of copper(+I) to yield thiocyanatoferrocene (1), and then the reaction of 1 with the Rupper-Prakash reagent and tetrabutylammonium fluoride (TBAF) to give 3 in an overall yield of 60%. This approach could be extended for the preparation of thiocyanato-(4) and trifluoromethylthio-ruthenocene (7), which are herein both reported for the first time. Interestingly, diferrocenyl disulfide (2a) and diruthenocenyl disulfide (5) could be isolated as side-products during the synthesis of 3 and 7, respectively. All new compounds were unambiguously characterized by 1 H, 13 C and 19 F NMR spectroscopy, mass spectrometry, cyclic voltammetry, elemental analysis as well by X-ray crystallography for 1, 4, 4b, 5, 6 and 7. 1-7 were then tested for their toxic activity on a cervical cancer (HeLa) and on a non-cancerous (MRC-5) cell lines. All organometallic compounds were found to be either not toxic or to have a moderate toxicity towards the cell lines used in this study.

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Nickel-Catalyzed Synthesis of Aryl Trifluoromethyl Sulfides at Room Temperature

Abstract: Inexpensive nickel-bipyridine complexes were found to be active for the trifluoromethylthiolation of aryl iodides and aryl bromides at room temperature using the convenient [NMe(4)][SCF(3)] reagent.

Cited by 330 publications

References 12 publications

Recent progress of high performance polymer OLED and OPV materials for organic printed electronics

Recent progress of high performance polymer OLED and OPV materials for organic printed electronics

Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides

Novel, Mercury-Free Synthetic Pathway for Trifluoromethylthio-Substituted Metallocenes

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