878376-35-3

Usage

Uses

Used in Chemical Synthesis:
PYRIDINE-2-SULFONYL FLUORIDE is used as a deoxyfluorination reagent for the conversion of primary and secondary alcohols into their corresponding fluorinated products. It offers a more efficient and selective method compared to other common deoxyfluorination reagents, such as DAST, which can exhibit more elimination side products on certain substrates.
Used in Pharmaceutical Industry:
PYRIDINE-2-SULFONYL FLUORIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those containing fluorinated moieties. Its broad substrate scope and thermal stability make it a valuable tool in the development of new drugs and drug candidates.
Used in Material Science:
PYRIDINE-2-SULFONYL FLUORIDE is used in the synthesis of fluorinated materials, which have unique properties such as increased hydrophobicity, chemical stability, and thermal resistance. These materials have potential applications in various industries, including coatings, textiles, and electronics.
Used in Environmental Applications:
PYRIDINE-2-SULFONYL FLUORIDE can be used in the development of environmentally friendly deoxyfluorination processes, which can help reduce the environmental impact of chemical synthesis and manufacturing. Its thermal stability and broad substrate scope make it a promising candidate for green chemistry applications.

InChI:InChI=1/C5H4FNO2S/c6-10(8,9)5-3-1-2-4-7-5/h1-4H

Upstream product

• 2637-34-5 2-Sulfanylpyridine 
• 66715-65-9 pyridine-2-sulfonyl chloride 

Downstream Products

• 5957-90-4 4-(2-pyridinyl)anisole 

Relevant academic research and scientific papers

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

PyFluor: A low-cost, stable, and selective deoxyfluorination reagent

We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [18F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.

A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols

Heteroaromatic thiols may be oxidized to the sulfonyl chloride at low temperature (-25 °C) by using 3.3 equiv of aqueous sodium hypochlorite. The reaction is rapid, avoids the use of chlorine gas, and succeeds with substrates that have previously been found to afford little or none of the sulfonamide product with other procedures. The method allows the preparation of the sulfonyl fluorides, which are stable enough to be purified and stored, making them potentially useful monomers in parallel chemistry efforts.