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Selectfluor

Selectfluor, chemically known as 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) and abbreviated as F-TEDA·2BF₄, is a crystalline, air- and moisture-stable salt with the molecular formula C₇H₁₄B₂ClF₉N₂, serving as a mild and versatile electrophilic fluorinating agent in organic chemistry.^[1]^[2] Developed between 1993 and 2004 by Professor R. Eric Banks at the University of Manchester in collaboration with Air Products and Chemicals, it was commercialized as a trademarked reagent and is now produced on an industrial scale of approximately 25 tonnes annually.^[3]^[4] This reagent is prized for its non-volatility, ease of handling, and safety profile compared to earlier fluorinating agents, enabling one-step introduction of fluorine with high regioselectivity across a broad range of substrates, including enol silanes, β-dicarbonyl compounds, and benzylic C-H bonds.^[1]^[5] Beyond fluorination, Selectfluor facilitates oxidative transformations, such as the conversion of sulfides to sulfoxides or sulfones and thiols to thiosulfonates under mild aqueous conditions, often achieving near-quantitative yields without additional catalysts.^[5] Its applications extend to pharmaceutical synthesis, notably in producing fluticasone derivatives used in blockbuster drugs like Advair for asthma and COPD treatment, contributing to over $17 billion in global sales from 2009 to 2012.^[3]

Overview and Properties

Chemical Structure

Selectfluor, known chemically as 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), is a dicationic salt with the common abbreviation F-TEDA·2BF₄.^[2]^[6] The molecule features a bicyclic core derived from 1,4-diazabicyclo[2.2.2]octane (DABCO), where both nitrogen atoms are quaternized to form the 1,4-diazoniabicyclo[2.2.2]octane framework, resulting in a positively charged dicationic system balanced by two tetrafluoroborate (BF₄⁻) counterions.^[2]^[6] Key functional groups include an N-chloromethyl (-CH₂Cl) substituent on one nitrogen and an N-F bond on the other, which are integral to its role as an electrophilic fluorinating agent.^[2]^[6] The rigid bicyclic structure, characterized by its bridged [2.2.2] geometry, constrains the nitrogen atoms and enhances the overall thermal and chemical stability of the N-F bond, facilitating efficient fluorine transfer in reactions.^[6] This structure can be notationally represented as a DABCO scaffold with the chloromethyl group attached to one bridgehead nitrogen and fluorine to the other, flanked by the BF₄⁻ anions, underscoring the symmetric yet functionalized dicationic core.^[2]

Physical and Chemical Properties

Selectfluor is a white to off-white crystalline solid, appearing as a free-flowing powder that is virtually non-hygroscopic, facilitating safe handling in laboratory settings.^[7] Its molecular formula is C₇H₁₄B₂ClF₉N₂, corresponding to a molar mass of 354.26 g/mol.^[8] The compound exhibits an apparent melting point around 190 °C, though its thermal behavior is complex, with exothermic decomposition occurring above 80 °C and literature noting some uncertainty in the exact value due to variability in measurement conditions.^[7] In terms of solubility, Selectfluor displays high solubility in polar solvents such as water (approximately 176 g/L at 20 °C) and acetonitrile, while it is only slightly soluble in methanol, ethanol, and acetone; it is insoluble in nonpolar solvents like hexane.^[7] This solubility profile stems from its ionic nature, enhanced by the bicyclic ammonium structure. Regarding stability, the reagent remains stable under dry conditions at room temperature, but it decomposes in moist environments or upon heating above 80 °C, potentially releasing hydrogen fluoride (HF).^[9]^[7] Storage is recommended at 2–8 °C under an inert atmosphere to prevent moisture-induced degradation, as it is sensitive to humidity despite its non-hygroscopic character.^[10] As a strong oxidant, Selectfluor possesses a reduction potential of approximately +0.33 V vs. saturated calomel electrode (SCE) in acetonitrile, enabling its role in electron-transfer processes while maintaining overall stability in aprotic media.^[11]

Synthesis

Laboratory Preparation

The laboratory preparation of Selectfluor, chemically known as 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), involves a three-step sequence starting from 1,4-diazabicyclo[2.2.2]octane (DABCO) as the bicyclic amine precursor.^[12] The process was first reported by Banks and colleagues in 1992, marking a key advancement in developing stable electrophilic fluorinating agents suitable for laboratory use.^[13]^[14] The initial step entails N-alkylation of DABCO with dichloromethane via a Menshutkin reaction to generate the chloromethylated intermediate, 1-(chloromethyl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride. This quaternization proceeds under mild conditions in an organic solvent, yielding the chloride salt as a known compound amenable to further manipulation.^[12] Subsequent ion exchange is achieved by treating the chloride salt (3.53 g, 17.9 mmol) with sodium tetrafluoroborate (1.97 g, 17.9 mmol) in dry acetonitrile (40 mL) at ambient temperature under a dry nitrogen atmosphere, with stirring overnight. The mixture is filtered to remove sodium chloride, and the solvent is evaporated to afford the tetrafluoroborate salt in 84% yield (3.75 g).^[12] The final fluorination step installs the critical N-F bond by reacting the tetrafluoroborate intermediate (1.01 g, 7.28 mmol) with elemental fluorine (neat, at 10–20 mmHg pressure) in dry acetonitrile (200 mL) at –35 °C until fluorine uptake ceases, typically requiring controlled delivery to maintain low temperature. The reaction mixture is filtered to remove sodium fluoride byproduct, and evaporation of the solvent provides Selectfluor as a white, free-flowing solid in 89% yield (2.20 g).^[12] The overall yield across the three steps is typically 70–80%, reflecting efficient conversion with minimal side reactions when conditions are optimized.^[14] Handling elemental fluorine demands specialized equipment, such as a closed fluorination apparatus with corrosion-resistant materials (e.g., Monel or Teflon) and rigorous safety protocols to mitigate risks of explosion or toxicity from undiluted F₂.^[12] While electrochemical fluorination methods have been explored as safer alternatives for analogous N-F compounds, the direct F₂-based protocol remains the primary laboratory route due to its simplicity and high efficiency. Flow chemistry adaptations have also been investigated for safer handling of F₂ in synthesis.^[14]^[15]

Commercial Availability

Selectfluor is a registered trademark originally owned by Air Products and Chemicals, Inc., now part of Versum Materials following a corporate spin-off in 2016, with subsequent acquisition by Merck KGaA in 2019.^[16]^[17] It is commercially available in purity grades of >95% F+ active for technical and general laboratory use, as well as >97–99% for analytical and high-precision applications.^[8]^[18]^[19] Major chemical distributors such as Sigma-Aldrich (Merck), Strem Chemicals, Thermo Fisher Scientific, and specialized fluorochemical providers supply Selectfluor in laboratory-scale quantities ranging from 5 g to 500 g.^[8]^[18]^[19] As of 2025 pricing trends, laboratory quantities cost approximately $40–$50 per 5 g and $100 per 25 g, scaling down proportionally for larger packs up to $700 for 500 g.^[20]^[18]^[21] Industrial production occurs on a multi-ton scale annually—estimated at around 25 tonnes globally as of 2015—employing optimized versions of laboratory preparation methods, with a focus on safe handling of fluorine gas (F₂) through controlled reactor systems to address its reactivity.^[4]^[22]^[15] Selectfluor is classified as a hazardous material, functioning as a strong oxidizer and self-heating solid (Class 4.2), and is subject to shipping restrictions under UN 3088 as a self-heating solid, organic, n.o.s. (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)), with Packing Group II requirements.^[19]^[10]

Reaction Mechanisms

Electrophilic Fluorination

Selectfluor serves as an electrophilic fluorinating agent in a polar two-electron process, where a nucleophilic substrate attacks the electrophilic fluorine atom bound to the nitrogen in the N-F moiety. This reaction proceeds via an S_N2-like displacement, with the substrate's nucleophilic site (such as an enolate carbon) directly bonding to the fluorine while the 1-(chloromethyl)-1,4-diazoniabicyclo[2.2.2]octane cation serves as the leaving group, often paired with a tetrafluoroborate anion.^[23]^[24] The general reaction can be represented as follows, typically requiring a base to generate the nucleophile from an acidic precursor:

\text{R-H} + \text{base} \rightarrow \text{R}^- + \text{H-base}^+ \\ \text{R}^- + \text{Selectfluor} \rightarrow \text{R-F} + \ce{[TEDA-CH2Cl]^{+} BF4^{-}}

This mechanism is supported by kinetic studies demonstrating second-order dependence on the concentrations of Selectfluor and the substrate, consistent with a bimolecular nucleophilic substitution.^[24] Evidence from radical clock experiments further corroborates the polar pathway, showing no rearrangement indicative of radical intermediates during fluorination of enolates, aromatics, and alkenes. The reagent's applicability spans enolates for α-fluorination of carbonyl compounds, electron-rich aromatics for ipso or ortho substitution, and alkenes for vicinal fluorofunctionalization under mild conditions, such as room temperature in polar solvents like acetonitrile or water.^[23]^[24] Selectfluor exhibits selectivity toward soft nucleophiles, such as enolates and π-systems in aromatics and alkenes, due to the polarized N-F bond that facilitates attack by less basic, more polarizable sites. Reactions typically occur under ambient conditions in polar aprotic or protic solvents, enabling high regioselectivity (e.g., α-position in carbonyls) without harsh reagents.^[24] However, the reagent is less effective with hard nucleophiles, such as simple alkoxides or amines, owing to mismatched electronics in the S_N2 transition state. Additionally, potential over-oxidation can arise if the substrate is prone to one-electron processes, though this is minimized in the classical polar regime by choosing appropriate solvents and additives.^[24]

Oxidative and Radical Pathways

Selectfluor participates in single-electron transfer (SET) processes as an oxidant, facilitating the generation of radical intermediates distinct from its two-electron electrophilic fluorination mode. In these pathways, Selectfluor undergoes reduction to form the radical dication TEDA²⁺ (N-(chloromethyl)-1,4-diazoniabicyclo[2.2.2]octane), which serves as a hydrogen atom transfer (HAT) or single-electron oxidant reagent.^[25] For instance, transition metals like Cu(I) or photocatalysts reduce Selectfluor via inner-sphere SET, enabling subsequent radical propagation.^[25] In radical fluorination, alkyl radicals abstract a fluorine atom from the N-F bond of Selectfluor, yielding the fluorinated product and TEDA²⁺. This process follows the general equation:

\text{R}^\bullet + \text{Selectfluor} \rightarrow \text{R-F} + \text{TEDA}^{\bullet+}

where TEDA^{\bullet+} represents the TEDA radical dication.^[25] Electron paramagnetic resonance (EPR) spectroscopy has confirmed the formation of such radical intermediates, including TEDA²⁺ and fluorine radicals, in light-mediated activations of Selectfluor.^[26]^[25] Beyond fluorination, Selectfluor enables two-electron oxidations unrelated to radical pathways. It converts primary and secondary alcohols to aldehydes, ketones, or carboxylic acids through hydride abstraction and oxygen insertion, often in the presence of iodide catalysts. Similarly, phenols bearing ortho- or para-hydroxy substituents are oxidized to quinones via sequential electron losses and tautomerization.^[27] Recent advancements since 2015 integrate Selectfluor with photoredox catalysis for deoxyfluorination of activated alcohols. Visible light excites Ir(III) complexes (e.g., Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆), which undergo oxidative quenching by Selectfluor to generate alkyl radicals from alcohol-derived oxalates; these radicals then capture fluorine from Selectfluor. Stern-Volmer quenching studies support this SET initiation, as Selectfluor efficiently quenches the photocatalyst excited state.^[28] Electrochemical activation has also emerged for C-H fluorination, where anodic oxidation of Selectfluor promotes radical C(sp³)-H abstraction, enabling site-selective fluorination of unactivated alkanes with nitrate additives.^[29] These methods complement the direct electrophilic fluorination detailed elsewhere.

Applications

General Fluorination Reactions

Selectfluor serves as a versatile electrophilic fluorinating agent for introducing fluorine into organic molecules through classical synthetic pathways, particularly in late-stage functionalization where mild conditions are essential. Since its introduction in 1994, it has become a cornerstone reagent for such transformations, enabling high regioselectivity and compatibility with diverse functional groups in aprotic solvents like acetonitrile or dichloromethane, often delivering yields of 70-95%.^[30]^[31] One primary application is the α-fluorination of carbonyl compounds, where Selectfluor reacts with enolates or silyl enol ethers to afford α-fluoro ketones and esters. For instance, β-dicarbonyl compounds, such as acyclic and cyclic 1,3-diketones or ketoesters, undergo efficient monofluorination at the α-position under mild conditions, typically in acetonitrile at room temperature, proceeding via an electrophilic mechanism that targets the enolizable site.^[30] Silyl enol ethers of ketones and aldehydes similarly provide α-fluorocarbonyls in high yields (up to 90%), with the reaction tolerant of ester, amide, and halide substituents. This method has been pivotal in synthesizing fluorinated intermediates for pharmaceuticals, where the fluorine enhances metabolic stability.^[31] Aromatic fluorination with Selectfluor targets electron-rich arenes, such as phenols, anilines, and anisoles, via electrophilic aromatic substitution to yield ortho- or para-fluoro derivatives. Phenols, for example, react selectively at the para position in acetonitrile, affording 4-fluorophenols in 80-95% yield without over-oxidation, owing to the reagent's controlled fluorine delivery. Anilines and N-protected anilines also undergo fluorination at electron-dense sites, maintaining compatibility with nitro or alkoxy groups. These reactions occur under ambient conditions, making Selectfluor preferable for sensitive aromatic scaffolds in natural product derivatization. For alkenes, Selectfluor facilitates addition reactions to form vicinal difluorides or fluorohydrins, depending on solvent polarity. In anhydrous acetonitrile, electron-rich or activated alkenes, like enol ethers or styrenes, yield 1,2-difluorides through anti addition, with yields exceeding 75% for substrates bearing ester or aryl groups. In aqueous media, such as wet acetonitrile, the same alkenes produce β-fluorohydrins via regioselective fluoronium ion formation followed by water trapping, achieving 70-90% yields and preserving double-bond geometry in cyclic systems. These transformations highlight Selectfluor's utility in building fluorinated motifs for bioactive molecules. Representative examples include the α-fluorination of steroid ketones, such as in progesterone derivatives, where Selectfluor selectively functionalizes the C-21 position in 85% yield, aiding in glucocorticoid analog synthesis. In carbohydrates, treatment of glycals with Selectfluor generates 2-deoxy-2-fluoro sugars via allylic fluorination, crucial for probing glycosidase inhibition in 80% yield. Natural products like alkaloids have also been fluorinated at enolizable sites, demonstrating the reagent's role in structure-activity relationship studies for drug discovery.^[31]

Specialized and Recent Applications

In recent years, Selectfluor has found specialized applications in photocatalytic processes, particularly for the deoxyfluorination of alcohols. A notable method involves visible-light photoredox catalysis using an iridium-based photocatalyst, such as [Ir(ppy)₂(dtbbpy)]PF₆, to convert activated secondary and tertiary alcohols—often as oxalate half-esters—into the corresponding alkyl fluorides. This approach proceeds via a radical-mediated C-F bond formation, achieving yields up to 85% for benzylic and allylic substrates under mild conditions in acetone-water mixtures, offering a metal-free alternative to traditional nucleophilic fluorination routes that minimizes elimination byproducts.^[28] Such light-driven strategies align with green chemistry principles by enabling room-temperature reactions without harsh reagents.^[32] Electrochemical methods have emerged in the 2020s for Selectfluor-enabled C-H fluorination, leveraging anodic oxidation to generate radicals for site-selective transformations. One high-impact protocol uses reticulated vitreous carbon electrodes with sodium nitrate as an initiator in acetonitrile, facilitating the fluorination of unactivated aliphatic C(sp³)-H bonds through a chain propagation involving Selectfluor as the fluorine donor. This batch-scalable process delivers yields of 50-78% for complex molecules like amino acids and terpenoids, with gram-scale demonstrations up to 100 g.^[33] Adaptations to continuous flow systems enhance safety and efficiency for industrial applications, particularly in late-stage functionalization of pharmaceuticals, reducing waste compared to stoichiometric oxidants.^[34] Selectfluor plays a pivotal role in the synthesis of fluorinated heterocycles via oxidative cyclization, with recent advances focusing on pyrimidines and indoles. For fluorinated pyrimidines, a recently reported Ag(I)-catalyzed method, as reviewed in 2025, employs Selectfluor to promote the cyclization of aminopyridines, yielding 5-fluoro-2-aminopyrimidines in 60-80% yields, regioselectively at the C5 position.^[35] In indole chemistry, a gold(I)-catalyzed tandem aminocyclization-fluorination of alkynes with Selectfluor generates 3,3-difluoroindoles in up to 90% yield, exploiting radical pathways for stereocontrol.^[35] These 2023-2025 developments, highlighted in comprehensive reviews, expand access to bioactive fluorinated motifs for drug discovery while emphasizing sustainable, catalyst-efficient conditions.^[36] Radical-mediated C-C bond formation using Selectfluor enables fluorinative couplings of alkenes with external radicals, providing difunctionalized products. A silver-catalyzed protocol (2017, extended in later works) involves decarboxylative addition of carboxylic acid-derived radicals to unactivated alkenes, followed by fluorination with Selectfluor, affording γ-fluorinated esters in 70-95% yields with anti-Markovnikov selectivity.^[37] More recent variants, such as arylhydrazine-derived radical additions (2019), achieve aryl-fluoralkyl couplings in 50-85% yields, with Selectfluor acting dually as oxidant and fluorine source to drive the radical chain.^[38] These methods highlight Selectfluor's versatility in constructing fluorinated carbon skeletons for materials and agrochemicals. Beyond fluorination, Selectfluor facilitates halide exchange for chlorination and iodination through oxidative activation. A 2023 protocol generates chlorinating species via chloride-for-fluoride exchange on Selectfluor, enabling late-stage chlorination of electron-rich arenes in 40-70% yields without metal catalysts.^[39] Similarly, a 2025 method uses Selectfluor to activate iodide or bromide for electrophilic aromatic halogenation, yielding iodoarenes in up to 92% with high regioselectivity.^[40] In Ritter-type reactions, Selectfluor variants promote amide formation from terpenes; for instance, a 2025 study on cedrol and cedrene under Ritter conditions with Selectfluor yields fluorinated amides in 60-80%, bypassing classical limitations by stabilizing carbocation intermediates.^[41] These applications underscore Selectfluor's role in green, multifunctional halogenations, addressing gaps in selective transformations for natural product derivatives.

Structural Analogs

Structural analogs of Selectfluor share the core bicyclic 1,4-diazoniabicyclo[2.2.2]octane framework with an N-F bond, but feature variations in substituents on the quaternary nitrogen or counterions to modulate reactivity and solubility.^[42] These modifications typically reduce the electrophilicity compared to the chloromethyl-substituted Selectfluor, enabling compatibility with more sensitive substrates.^[42] F-TEDA variants, such as Selectfluor II, replace the chloromethyl group with hydrogen or other less electron-withdrawing substituents, often paired with bis(trifluoroacetate) or hexafluorophosphate counterions to provide milder fluorination conditions. This analog, developed in the early 1990s as part of efforts to expand the N-F reagent family, exhibits lower reactivity toward electron-rich systems while maintaining stability. For instance, the bis(trifluoroacetate) salt enhances handling by reducing hygroscopicity, allowing applications in aqueous media where the original BF₄⁻ version might decompose.^[42] Accufluor (NFTh), introduced in 1995, is another close N-F analog featuring a hydroxy substituent at the 1-position instead of chloromethyl, with bis(tetrafluoroborate) counterions that improve solubility in polar solvents. This structural tweak diminishes the electron-withdrawing effect on the N-F bond, resulting in selective fluorofunctionalization under ambient conditions, particularly for alkenes prone to over-oxidation.^[43] DABCO-based derivatives include N-fluoroquinuclidinium salts, which adapt the bicyclic architecture by using a single nitrogen bridge (1-azabicyclo[2.2.2]octane core) and varying counterions like fluoride or triflate, with some later variants altering bridge lengths for tuned steric properties. Originating from foundational work in 1986, these evolved in the late 1990s to address substrate-specific needs, such as improved selectivity in aromatic fluorinations.^[42] Key differences across these analogs lie in leaving group variations—e.g., acetate or trifluoroacetate versus BF₄⁻—which influence nucleophilic displacement rates and overall fluorination efficiency.^[42]

Alternative Fluorinating Agents

N-fluorobenzenesulfonimide (NFSI), an amide-based electrophilic fluorinating agent, provides a milder alternative to Selectfluor for introducing fluorine into nucleophilic substrates such as enolates and silyl enol ethers, often achieving moderate to high yields under catalysis-free conditions or with transition metals like titanium.^[44] Unlike Selectfluor, which exhibits higher reactivity and can lead to over-oxidation, NFSI operates via a less aggressive N-F bond transfer mechanism, making it particularly suitable for sensitive carbanions and aromatic C-H fluorinations in aqueous media or photocatalysis, with yields up to 87% reported in recent metal-free protocols.^[45] However, NFSI requires higher temperatures or neat conditions for less activated substrates and shows lower fluorinating power compared to Selectfluor, limiting its use in rapid or broad-scope reactions. For nucleophilic fluorination, particularly the conversion of alcohols to alkyl fluorides (deoxyfluorination), Deoxo-Fluor (bis(2-methoxyethyl)aminosulfur trifluoride) serves as a versatile reagent that replaces oxygen with fluorine under mild conditions, offering broader substrate compatibility than earlier analogs like DAST.^[46] This liquid agent excels in transforming primary and secondary alcohols, as well as carbonyls to gem-difluorides, with good to excellent yields and facile purification, though it reacts exothermically with water to generate HF, necessitating careful handling in inert atmospheres.^[46] In contrast to Selectfluor's electrophilic mode, Deoxo-Fluor acts via nucleophilic attack, avoiding oxidative side products but producing more elimination in hindered systems.^[47] XtalFluor, available as crystalline salts like XtalFluor-E (diethylaminodifluorosulfinium tetrafluoroborate), addresses some hazards of Deoxo-Fluor by providing enhanced thermal stability (decomposition above 200°C) and easier handling as a solid, ideal for deoxyfluorination of alcohols and gem-difluorination of carbonyls when paired with promoters like Et₃N·3HF.^[47] It delivers higher selectivity (e.g., 12:1 fluoride-to-elimination ratio for cyclooctanol) and reduced HF release compared to liquid nucleophilic agents, though it remains more hazardous and corrosive than electrophilic options like Selectfluor due to its HF-derived nature.^[47] Cost-effective synthesis and commercial availability make XtalFluor preferable for large-scale deoxyfluorinations, but its scope is narrower, focusing on oxygen-containing functional groups rather than C-H activations.^[48] Elemental fluorine (F₂) and HF derivatives represent early, gas-phase or highly corrosive alternatives for direct fluorination, capable of perfluorinating hydrocarbons or activating aromatics with high efficiency on industrial scales.^[49] However, their extreme reactivity leads to poor selectivity, over-fluorination, and significant safety risks, including explosions and toxicity, prompting avoidance in modern laboratory synthesis in favor of stable, solid N-F reagents like Selectfluor.^[49] Selectfluor is often preferred for its superior selectivity in electrophilic and radical fluorinations across diverse substrates, minimizing side reactions compared to NFSI's milder profile or the corrosiveness of nucleophilic agents like Deoxo-Fluor and XtalFluor, which excel in cost-sensitive deoxyfluorinations but pose handling challenges. Alternatives like NFSI shine in photocatalyzed or enolate-specific transformations due to their redox neutrality, while elemental F₂ suits only specialized, controlled applications.^[50] Post-2020 trends emphasize greener shifts toward electrochemical, photocatalytic, and mechanochemical methods using these reagents in water or flow systems, reducing solvent use and waste, yet Selectfluor's versatility ensures its continued prominence in versatile syntheses.^[50]

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Silver-catalyzed radical carbofluorination of unactivated alkenes ...
Jan 18, 2017 · The AgNO3-catalyzed reactions of unactivated alkenes with acetic acid and Selectfluor reagent in aqueous solution afforded the corresponding γ- ...
[38]
Radical Carbofluorination of Alkenes With Arylhydrazines ... - PubMed
Feb 21, 2019 · Radical carbofluorination reactions starting from arylhydrazines and nonactivated alkenes, in which the C-F bond is formed through the use ...Missing: mediated | Show results with:mediated
[39]
Selectfluor‐Mediated Chlorination and Fluorination of Arenes: Late ...
Apr 23, 2023 · Comparable halogen exchange reactions on Selectfluor (1) are known for bromide and iodide, but have not yet been reported for chloride.Abstract · Introduction · Results and Discussion · Conclusions
[40]
Selectfluor-promoted electrophilic aromatic halogenation: a general ...
Sep 29, 2025 · Selectfluor-promoted electrophilic aromatic halogenation: a general strategy for iodination and bromination via oxidative halide activation.
[41]
Selectfluor-mediated transformation of cedrol and cedrene under the ...
In this work, the Selectfluor-mediated transformation of cedrol and cedrene under the Ritter reaction conditions is presented for the first time.
[42]
https://doi.org/10.3762/bjoc.17.123
[43]
N-Fluorobenzenesulfonimide: a useful and versatile reagent for the ...
This review updates recent advances and developments in the direct fluorination and amination of (hetero)aromatic C–H bonds utilizing N- ...
[44]
Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum ...
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the ...
[45]
Aminodifluorosulfinium Salts: Selective Fluorination Reagents with ...
Apr 21, 2010 · Crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues.
[46]
https://pubs.rsc.org/en/content/articlelanding/1999/cc/a808517j
[47]
Application of elemental fluorine in organic synthesis
Selective fluorination of 1-hydroxyisoquinolines using Selectfluor™. ... Elemental Fluorine and HOF·CH 3 CN in Service of General Organic Chemistry.
[48]
Catalytic Fluorination with Modern Fluorinating Agents - MDPI
One of the main advantages of Selectfluor is its ability to selectively fluorinate electron-rich nucleophilic centers under mild conditions. This compound is ...