Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3-triazole and their derivatives as energetic materials by click chemistry.

1-Pentafluorosulfanyl acetylene and its derivatives react with azide or diazomethane giving rise to an SF5-substituted 1,2,3-triazole or pyrazole. The SF5 group increases density remarkably and as a result enhances the detonation performance of the energetic materials relative to the CF3 group.

• Publication year

  2007

• Venue

  Organic Letters

• Publication date

  2007-08-23

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/OL701602APMID 17715932
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Rapid and accurate estimation of densities of room-temperature ionic liquids and salts.

  2007cited by this paper
• Synthesis of novel pentafluorosulfanylfurans. Two retro-Diels-Alder approaches.

  2006cited by this paper
• Pentafluoronitrosulfane, SF5NO2.

  2006cited by this paper
• Synthesis of the long sought after compound pentafluoronitrosulfane, SF5NO2.

  2006cited by this paper
• A new synthesis of pentafluorosulfanylbenzene.

  2004cited by this paper
• New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds.

  2002cited by this paper
• A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.

  2002cited by this paper
• Difluorooxymethylene-Bridged Liquid Crystals: A Novel Synthesis Based on the Oxidative Alkoxydifluorodesulfuration of Dithianylium Salts.

  2001cited by this paper
• Pentafluorosulfanylnitramide salts.

  2000cited by this paper
• Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

  1988cited by this paper

• Intramolecular Multifunctionalization in a Fused N ‐Rich Scaffold Produces a Record‐Density CF 3 Energetic

  2026cites this paper
• Synthesis and Reaction of Pentafluorosulfanyl Chloride (SF5Cl)

  2025cites this paper
• Employing Nitrogen-Sulfur Synergy: 1,2,3-Triazole-Thiadiazole-Based Energetic Materials.

  2025cites this paper
• Fluorinated B-phenylated scorpionates as tunable platforms for stabilizing thallium(I) and silver(I)-ethylene complexes.

  2025cites this paper
• Nitrogen-rich triazine, triazolo and tetrazolo-triazine-based energetic compounds: A new class of fluorinated organic explosives

  2025cites this paper
• Role of -SF5 Groups in Modulating the Stability and Energy Characteristics of Fluorinated Molecules

  2025cites this paper
• Simultaneous hydroxido-, nitrato-, and phenoxido-bridged binuclear copper Schiff base complex for green catalytic click chemistry: Synthesis, structure, Hirshfeld surface analysis, theoretical study and photoluminescence spectra

  2024cites this paper
• 1,3-Dipolar Cycloaddition of SF5-Alkynes with Nonstabilized Diazo: Synthesis of Highly Substituted SF5-3H-Pyrazoles.

  2024cites this paper
• Advancing energetic chemistry: the first synthesis of sulfur-based C-C bonded thiadiazole-pyrazine compounds with a nitrimino moiety.

  2024cites this paper
• Synthesis of Substituted Pentafluorosulfanylpyrazoles Under Flow Conditions.

  2024cites this paper
• Transition-metal-free synthesis of (Z)-N1-vinyl-benzotriazoles from 1-arylmethylbenzotriazoles and arylaldehydes

  2023cites this paper
• Hydroamination of Triisopropylsilyl Acetylene Sulfur Pentafluoride - a Bench-top Route to Pentafluorosulfanylated Enamines.

  2023cites this paper
• Synthesis and characterization of 2-amino-4,5-bis(tetrazol-5-yl)-1,2,3-triazole: A high-nitrogen energetic material with low sensitivities and high thermal stability

  2023cites this paper
• Synthesis and further use of SF5-alkynes as platforms for the design of more complex SF5-containing products

  2022cites this paper
• Applications of 2-Oxoaldehydes

  2022cites this paper
• Synthesis and application of pentafluorosulfanylation reagents and derived aliphatic SF5-containing building blocks

  2022cites this paper
• Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions

  2022cites this paper
• Pyrazole Derivative Containing Naphthalene Moiety: Cytotoxocity (Breast and Cervical Cancer), Antibacterial and Antifungal Studies Using Experimental and Theoretical Tools

  2022cites this paper
• Efficient synthesis of celecoxib and pyrazole derivatives on heterogeneous Ga-MCM-41-SO3H catalyst under mild condition

  2022cites this paper
• Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process

  2022cites this paper
• The radical reaction of ethynylbenziodoxolone (EBX) reagents with pentafluorosulfanyl chloride: new approach to SF5-substituted alkynes

  2022cites this paper
• Synthesis and characterization of a novel hydroxy telechelic polyfluoroether to enhance the properties of HTPB solid propellant binders

  2022cites this paper
• Power of Sulfur – Chemistry, Properties, Laser Ignition and Theoretical Studies of Energetic Perchlorate-Free 1,3,4-Thiadiazole Nitramines

  2022cites this paper
• Synthesis and energetic properties of trifluoromethyl-substituted 2-nitro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives

  2021cites this paper
• Synthesis of vinyl-1,2,3-triazole derivatives under transition metal-free conditions

  2021cites this paper
• 4,5-Dicyano-1,2,3-Triazole—A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures

  2021cites this paper
• Synthetic advances in C(sp 2)-H/N–H arylation of pyrazole derivatives through activation/substitution

  2021cites this paper
• Synthesis and characterization of a novel fluorine-containing triblock copolymer as a potential binder

  2021cites this paper
• Synthesis and characterization of a novel fluorine-containing copolymer P(FPO/NIMMO) as a potential energetic binder

  2021cites this paper
• Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues.

  2021cites this paper
• Ring Opening of Epoxides and Aziridines with Benzotriazoles Using Magnetically Retrievable Graphene Based (CoFe@rGO) Nanohybrid

  2021cites this paper
• Selective Synthesis of Bis(3-(3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl)-4,4'-azo- and -azoxyfurazan Derivatives.

  2021cites this paper
• Recent approaches towards one-carbon homologation-functionalization of aldehydes.

  2021cites this paper
• Incorporation of the pentafluorosulfanyl group through common synthetic transformations

  2021cites this paper
• A Brief Review on Antimicrobial Potential of Pyrazoles (From 2010-2018)

  2020cites this paper
• Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa

  2020cites this paper
• Pyridine tetrafluoro-λ6-sulfanyl chlorides: spontaneous addition to alkynes and alkenes in the presence or absence of photo-irradiation

  2020cites this paper
• Materials applications of organofluorine compounds

  2020cites this paper
• The Thermochemistry and Initial Decomposition Pathways of Triazole Energetic Materials.

  2020cites this paper
• HBF4/ACN: A simple and efficient protocol for the synthesis of pyrazoles under ambient reaction conditions

  2020cites this paper
• Computational study of energetic derivatives of 3,3′-bridged ditriazoles

  2020cites this paper
• A Method Suitable for Predicting the Crystal Densities of Cyclic Organic Fluorides

  2020cites this paper
• Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal-organic framework Co(4,4'-bipyrazolate).

  2020cites this paper
• Fluorinated Pyrazoles: From Synthesis to Applications.

  2020cites this paper
• High energy density materials based on fluorinated bridged trinitromethyl azo triazole derivatives: a quantum chemical study of thermodynamic and energetic properties

  2020cites this paper
• Synthesis of substituted dihydro-1H-pyrazoles and 1H-pyrazoles via formal [4+1] annulation of α-arylhydrazonoketones and dimethyl sulfonium methylides

  2019cites this paper
• Surface plasmon resonances enhanced click chemistry through synergistic photothermal and hot electron effects.

  2019cites this paper
• An Unexpected Method to Synthesize Fluorinated Derivative of ANPZ

  2019cites this paper
• SO 3 Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction

  2019cites this paper
• Synthesis of N-Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives.

  2019cites this paper
• A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study

  2019cites this paper
• Synthesis of aryl and heteroaryl tetrafluoro-λ6-sulfanyl chlorides from diaryl disulfides using trichloroisocyanuric acid and potassium fluoride

  2019cites this paper
• Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines.

  2018cites this paper
• Synthesis of Biologically Relevant Heterocycles in Aqueous Media

  2018cites this paper
• Copper(II)-dipicolinate-mediated clickable azide–alkyne cycloaddition in water as solvent

  2018cites this paper
• A nitrogen-rich ligand as a scaffold for slow magnetic relaxation in dysprosium-based 0D and 1D architectures.

  2018cites this paper
• Effect of Fluoro Substituents on Polynitroarylenes: Design, Synthesis and Theoretical Studies of Fluorinated Nitrotoluenes.

  2018cites this paper
• In Situ Generation of Copper Nanoparticles by Rongalite and Their Use as Catalyst for Click Chemistry in Water

  2018cites this paper
• SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME 1,4- AND 1,4,5-SUBSTITUTED-1H-1,2,3TRIAZOLES IN RELATION TO THE STAPHYLOCOCCUS AUREUS STRAIN

  2018cites this paper
• An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ6-sulfanyl triazoles

  2018cites this paper
• Cellulose supported poly(amidoxime) copper complex for Click reaction

  2017cites this paper
• Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.

  2017cites this paper
• Enthalpies of Formation of Hydrazine and Its Derivatives.

  2017cites this paper
• Theoretical design and characterisation on the fluorinated nitrophenyl azidotriazoles

  2017cites this paper
• Syntheses and Applications of Trifluoromethyl- and Pentafluorosulfanyl-Containing Organic Molecules

  2017cites this paper
• Silver nanoparticles supported over Al2O3@Fe2O3 core-shell nanoparticles as an efficient catalyst for one-pot synthesis of 1,2,3-triazoles and acylation of benzyl alcohol

  2017cites this paper
• Synthesis of 5-pentafluorosulfanyl indazoles

  2017cites this paper
• Recent advancements in the synthesis of pentafluorosulfanyl (SF 5 )-containing heteroaromatic compounds

  2017cites this paper
• Biosourced cyclosophoraose-driven acceleration of click reaction in H2O

  2017cites this paper
• Synthetic Methods for High-Energy Organofluorine Compounds

  2017cites this paper
• Solubility Thermodynamics of Organic Energetic Materials

  2017cites this paper
• A heteropolyacid-based ionic liquid immobilized onto magnetic fibrous nano-silica as robust and recyclable heterogeneous catalysts for the synthesis of tetrahydrodipyrazolopyridines in water

  2016cites this paper
• Synthesis of nitrate ester and nitramine derivatives of polyfluoro alkyl compounds for high energy materials

  2016cites this paper
• Iron(III) phthalocyanine chloride-catalyzed oxidation–aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles

  2016cites this paper
• New organometallic Schiff-base copper complexes as efficient “click” reaction precatalysts

  2016cites this paper
• Synthesis, crystal structures and thermal stabilities of zinc coordination polymers containing the 3-hydrazino-4-amino-1,2,4-triazole ligand

  2016cites this paper
• Importance of a Fluorine Substituent for the Preparation of meta- and para-Pentafluoro-λ(6) -sulfanyl-Substituted Pyridines.

  2016cites this paper
• SF5-Substituted Aromatic Heterocycles

  2016cites this paper
• The Synthesis and Biological Evaluation of N‐Substituted 1H‐Benzimidazol‐2‐yl‐1H‐pyrazole‐3,5‐diamines

  2016cites this paper
• ,-DIBROMOKETONES AS USEFUL PRECURSORS IN ORGANIC SYNTHESIS: A SIMPLE AND EFFICIENT SYNTHESIS OF 2,4-DIARYL- 1,2,3-TRIAZOLES VIA OXIDATIVE CYCLIZATION OF BISPHENYLHYDRAZONES

  2016cites this paper
• Formation of α-SF5-Enolate Enables Preparation of 3-SF5-Quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-Pyridin-2-ones: Evaluation of their Physicochemical Properties.

  2016cites this paper
• Study of thermal decomposition mechanisms and absorption cross section of nitro-rich phenyl- and bis-series 1,2,3-triazoles.

  2016cites this paper
• Formal [4 + 1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles.

  2016cites this paper
• Brönsted acid-mediated annulations of 1-cyanocyclopropane-1-carboxylates with arylhydrazines: efficient strategy for the synthesis of 1,3,5-trisubstituted pyrazoles

  2016cites this paper
• Advances of azide-alkyne cycloaddition-click chemistry over the recent decade

  2016cites this paper
• Synthesis, Characterization, and Energetic Studies of Polynitro Aryl‐1,2,3‐2 H‐Triazoles

  2016cites this paper
• Evaluation of thermal stability and time resolved acoustic fingerprint spectra of 1-(2-methoxy,-3,5-dinitrophenyl)-1H-1,2,3-triazole

  2016cites this paper
• Preparation and utility of organic pentafluorosulfanyl-containing compounds.

  2015cites this paper
• Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations

  2015cites this paper
• Synthesis and structure of 1-tert-butyl-substituted 3(5)-alkylpyrazoles from 2-chlorovinyl ketones

  2015cites this paper
• Carboxymethylpullulan promoted Cu2O-catalyzed Huisgen-click reaction

  2015cites this paper
• Cu(OAc)2·H2O—an efficient catalyst for Huisgen-click reaction in supercritical carbon dioxide

  2015cites this paper
• Polymer anchored ruthenium complex: A highly active and recyclable catalyst for one-pot azide–alkyne cycloaddition and transfer-hydrogenation of ketones under mild conditions

  2015cites this paper
• Highly efficient click reaction on water catalyzed by a ruthenium complex

  2015cites this paper
• One-step synthesis of azole- and benzazole-based sulfonamides in aqueous media

  2015cites this paper
• Ambient benzotriazole ring opening through intermolecular radical addition to vinyltriazole.

  2015cites this paper
• Use of 1-pentafluorosulfanyl-phenylacetylenes for the preparation of SF5-substituted five-membered ring heterocycles through 1,3-dipolar cycloadditions. Isoxazoles and isoxazolines

  2015cites this paper
• Synthesis and characterization of 2-pyridylsulfur pentafluorides.

  2015cites this paper
• Synthesis of highly diversified 1,2,3-triazole derivatives via domino [3 + 2] azide cycloaddition and denitration reaction sequence

  2015cites this paper
• Aqua mediated multicomponent reaction under phase transfer catalysis: A novel and green approach to access fused pyrazoles

  2015cites this paper