6462-50-6

Upstream product

• 1146-42-5 p-methoxyphenylsulfonothioic phenyl ester 
• 123-54-6 acetylacetone 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 696-62-8 para-iodoanisole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 696-63-9 4-Methoxybenzenethiol 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-66-3 methoxybenzene 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 100146-08-5 1,2-Bis-<4-methoxy-phenylsulfon>-1,2-dicyan-ethen 
• 64326-50-7 3-(4-methoxyphenylsulfonyl)acrylonitrile 
• 38568-57-9 1-Methoxy-1-(4-methoxy-benzenesulfonyl)-propan-2-one 
• 59830-33-0 1-(p-methoxyphenylsulfonyl)-2-methyl-4-acetoxy-but-2-ene 
• 38944-90-0 C₁₀H₁₃NO₃S₂ 
• 24225-04-5 p-methoxybenzenesulfonyl cyanide 
• 78676-07-0 2-(4-Methoxy-benzenesulfonyl)-1-(5-nitro-furan-2-yl)-ethanone 
• 5285-90-5 4-thiocyanatoanisole 
• 80120-69-0 C₈H₇NO₃S₂ 
• 102837-24-1 (R)-2-Amino-3-(4-methoxy-benzenesulfonylsulfanyl)-propionic acid 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 
• 114971-47-0 Sodium; 4-methoxy-benzenethiosulfonate 
• 41024-54-8 2-(4-methoxyphenylsulfonyl)-1-phenylethanone 
• 85870-06-0 1-(4-Methoxy-benzenesulfonyl)-propan-2-ol 

Relevant academic research and scientific papers

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.

Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I

A wide range of N-unsubstituted enaminosulfones were obtained via electrochemical sulfonylation of vinyl azides with sulfonyl radicals generated from sodium sulfinates. The discovery of N-unsubstituted enaminosulfones synthesis is based on a unique ability of the azido group to eliminate the N2 molecule. The process is performed under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode applying NH4I both as the redox catalyst and the supporting electrolyte.

Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process

Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (～1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.