- Pd-catalyzed direct arylation of nitro(pentafluorosulfanyl)benzenes with aryl bromides
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Limited methods for the synthesis of SF5-substituted compounds significantly restrict their widespread application. A Pd-catalyzed direct arylation of nitro(pentafluorosulfanyl)benzenes with aryl bromides is reported. This protocol provides a facile and straightforward access to diversified SF5-containing aryl derivatives. The notable features of this reaction are its synthetic simplicity, high reaction efficiency, and good regioselectivity.
- Wang, Chao,Yu, Yan-Bo,Fan, Shilu,Zhang, Xingang
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- The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine
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The trifluoromethyl group of fluoxetine 1 and fenfluramine and norfenfluramine, 2 and 3, was substituted by the pentafluorosulfanyl group. On examination of the efficacy of the pentafluorosulfanyl containing compounds as inhibitors of 5-hydroxytryptamine receptors, it was found that substitution could lead to enhanced selectivity and in the case of the pentafluorosulfanyl analog of fenfluramine, 18, it significantly enhanced potency against the 5-HT2b, 5-HT2c, and 5-HT6 receptors.
- Welch, John T.,Lim, Dong Sung
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Read Online
- Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects
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Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.
- Ajenjo, Javier,Klepetá?ová, Blanka,Greenhall, Martin,Bím, Daniel,Culka, Martin,Rulí?ek, Lubomír,Beier, Petr
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supporting information
p. 11375 - 11382
(2019/08/20)
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- METHOD FOR PRODUCING NITROGEN-CONTAINING PENTAFLUOROSULFANYLBENZENE COMPOUND
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A method for producing a nitrogen-containing pentafluorosulfanylbenzene compound of formula (2a) or (2b): (wherein R1 a hydrogen atom or a hydrocarbon group; Z is an aryl group linked to a carbonyl group; Y is a group of formula (Y1), (Y2), (Y3), or (Y4); R2 is a hydrogen atom or a hydrocarbon group) the method comprising reacting a halogeno-pentafluorosulfanylbenzene compound of formula (1) with a nitrogenous nucleophile: (wherein X is a halogen atom; n is an integer of 1 to 5; R1 is as defined above).
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Paragraph 0077; 0078; 0079; 0080; 0081
(2018/01/11)
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- PENTAFLUOROSULPHOLANE-CONTAINING ANTIDIABETIC COMPOUNDS
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This invention provides for certain pentafluorosulpholane-containing compounds of the formula or a pharmaceutically acceptable salt, ester, solvate or prodrug thereof, wherein the variables are defined herein; the inventive compounds are agonists of the G
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Page/Page column 49-50
(2010/08/08)
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- Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives. X-ray structure of 3-SF5-C6H4-COOH
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The high yield synthesis of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives is described starting from the NO2-derivatives, which are reduced to the corresponding anilines. Then the NH2- group is converted to bromide and subsequently to the HC{double bond, long}O moiety. The benzaldeydes are then oxidised to the corresponding benzoic acids. The X-ray structure of 3-SF5-C6H4-COOH is also reported.
- Zarantonello,Guerrato,Ugel,Bertani,Benetollo,Milani,Venzo,Zaggia
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p. 1449 - 1453
(2008/09/18)
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- METHOD FOR PRODUCING 4-PENTAFLUORIDE-SULFANYL-BENZOYLGUANIDINES
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The invention relates to a method for producing 4-pentafluoride-sulfanyl-benzoylguanidines of formula (I) wherein groups from R1 to R4 correspond to meanings given in claims. The compounds of the formula (I) constitute NHE1 inhibitors and can be used for
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Page/Page column 18
(2008/06/13)
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- PENTAFLUOROSULFANYL BENZOYLGUANIDINES, METHOD FOR THEIR PRODUCTION, THEIR USE AS MEDICAMENTS OR DIAGNOSTIC AGENTS AND MEDICAMENT CONTAINING THE SAME
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The invention relates to pentafluorosulfanyl benzoylguanidines of formula (I), in which R1 to R4 are defined as cited in the claims. Said substances are suitable for use as anti-arrhythmic medicaments comprising cardio-protective components for the prophylaxis and treatment of infarcts, in addition to the treatment of angina pectoris. They also preventatively inhibit the pathophysiological events that occur during ischaemically induced traumas, in particular during the triggering of ischaemically induced cardiac arrhythmia.
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Page/Page column 36
(2008/06/13)
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- ORTHO-SUBSTITUTED PENTAFLUORIDE SULFANYL-BENZENES, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF IN THE FORM OF VALUABLE SYNTHESIS INTERMEDIATE STAGES
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The invention relates to pentafluoride-sulfanyl-benzenes of formula (I), wherein groups from R1 to R5 correspond to meanings given in claims and constitute valuable intermediates, for example for producing drugs, diagnosis agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.
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Page/Page column 20; 21
(2010/02/11)
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- Synthesis of some arylsulfur pentafluoride pesticides and their relative activities compared to the trifluoromethyl analogues
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Examples of pesticides containing an arylsulfur pentafluoride group were made and their biological activities compared to the corresponding trifluoromethyl analogues. A phenylsulfur pentafluoride analogue of the insecticide fipronil, screened against a resistant strain of Musca domestica, showed higher activity than the corresponding trifluoromethyl analogue.
- Crowley, Patrick J.,Mitchell, Glynn,Salmon, Roger,Worthington, Paul A.
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p. 138 - 142
(2007/10/03)
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- A new method for the synthesis of aromatic sulfurpentafluorides and studies of the stability of the sulfurpentafluoride group in common synthetic transformations
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A new synthesis of aromatic sulfurpentafluoride compounds is described. Subsequent elaboration of the aromatic rings in the presence of the sulfurpentafluoride group is also discussed for a variety of common synthetic methods. This paper also describes ab initio electronic structure calculations of 3- and 4-aminophenylsulfurpentafluoride, compared with 3- and 4-aminobenzotrifluoride, and presents X-ray crystal structures of two aromatic sulfurpentafluoride derivatives. (C) 2000 Elsevier Science Ltd.
- Bowden, Roy D.,Comina, Paul J.,Greenhall, Martin P.,Kariuki, Benson M.,Loveday, Amanda,Philp, Douglas
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p. 3399 - 3408
(2007/10/03)
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- Liquid crystals based on hypervalent sulfur fluorides: Pentafluorosulfuranyl as polar terminal group
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The somewhat 'exotic' pentafluorosulfuranyl functionality is one of the strongest electron-withdrawing groups with a purely inductive effect owing to its chemical stability and the resulting high dipole moment of its aromatic derivatives, this group was crucial to the design and synthesis of a new class of highly polar liquid crystals (such as 1) for application in active matrix displays. A computational model was developed with the aim to understand and predict the electrooptic properties of liquid crystals based on hypervalent sulfur fluorides.
- Kirsch, Peer,Bremer, Matthias,Heckmeier, Michael,Tarumi, Kazuaki
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p. 1989 - 1992
(2007/10/03)
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- Heterocyclic compounds and insecticidal use
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Compounds with insecticidal activity have the formula (I): STR1 wherein R1 is hydrogen, halogen, or a group NR4 R5 wherein R4 and R5 are independently selected from hydrogen or alkyl; R2 is a group --S(O)n R6 wherein n is 0, 1 or 2 and R6 is a haloalkyl group; R3 is --CN or is a group CX--NY1 Y2 for example --CS--NH2 ; and R7 and R8 , which may be the same or different, are halogen.
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