Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates

Billard, Thierry; Large, Sylvie; Langlois, Bernard R.

doi:10.1016/s0040-4039(96)02216-2

Cited by 189 publications

(75 citation statements)

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“…These includes oxidative trifluoromethylthiolation of terminal alkynes with CF 3 SiMe 3 , and elemental sulphur 42 or later with AgSCF 3 , 43 copper-catalyzed trifluoromethylthiolation of terminal alkynes with a novel thioperoxy reagent, 25 base-catalyzed trifluoromethylthiolation of terminal alkynes with a trifluoromethanesulfenamide reagent, 44 and bismuth(III)promoted trifluoromethylthiolation of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide reagent. [46][47][48][49][50][51][52] The organoselenium compounds also display significant potential as antioxidant, antitumor, antimicrobial, and antiviral agents. This probably because the starting materials and reagents are either highly toxic, unstable, commercially unavailable, or require elaborate preparative methods.…”

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confidence: 99%

Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

2015

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Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

2015

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“…Cyanoferrocene (2b) could also be found in trace amounts as a minor side-product. 31 The desired compound 3 was obtained by treating 1 with an excess of the commercially available Ruppert-Prakash reagent (Me 3 SiCF 3 ) and a catalytic amount of a tetrabutylammonium fluoride solution in THF using slightly different conditions to those reported by Langlois et al [32][33][34] 3 was obtained as a yellow oil in excellent yield (90%) and the spectroscopic data matched those previously described by Metzler-Nolte et al Encouraged by the promising results obtained for 3 and the importance of small functionalized metallocenes, 35 we decided to investigate the possibility to prepare ruthenocenyl analogues of 1 and 3. Of note, ruthenocene derivatives were shown, over the last years, to have interesting biological properties and to be an interesting surrogate for ferrocenyl derivatives to understand the mechanism of action of these ferrocenyl compounds.…”

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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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“…There are many methods about the synthesis of aryltrifluoromethylsulfides [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Thereinto, the reaction of aryl disulfide with trifluoromethyl bromide in the presence of sulfoxylate anion radical precursors developed by Wakselman et al [23,24] constitute an important method of synthesis.…”

Section: Resultsmentioning

confidence: 99%

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

Tang

Zhong

Lin

2007

Journal of Fluorine Chemistry

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Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates

Cited by 189 publications

References 11 publications

Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

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

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

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