775-27-9

Upstream product

• 150-76-5 4-methoxy-phenol 
• 640723-20-2 fluorosulfonyl fluoride 
• 1139705-25-1 4-methoxyphenyl 1H-imidazole-1-sulfonate 

Downstream Products

• 17113-31-4 2-(4-methoxyphenyl)furan 
• 121-98-2 methyl 4-methoxybenzoate 
• 637-69-4 4-Methoxystyrene 
• 613-37-6 4-methoxylbiphenyl 
• 94-30-4 ethyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 874-90-8 4-methoxybenzonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-66-3 methoxybenzene 
• 795-44-8 4-(diphenylphosphoryl)benzonitrile 
• 3762-33-2 diethyl (p-methoxyphenyl)phosphonate 
• 3762-32-1 dibutyl (4-methoxyphenyl)phosphonate 
• 17171-17-4 4'-methoxy-3-methylbiphenyl 

Relevant academic research and scientific papers

Nickel- and Palladium-Catalyzed Cross-Coupling of Aryl Fluorosulfonates and Phosphites: Synthesis of Aryl Phosphonates

The synthesis of aryl phosphonates via nickel and palladium-catalyzed cross-coupling of aryl fluorosulfonates and phosphites is described. The products were obtained in good to excellent yields under mild conditions with broad functional group compatibility, employing either Pd(OAc)2 and DPEPhos or the readily available NiCl2(dme) and Xantphos as catalytic systems. Noteworthily, the present C(sp2)?P bond formation method could be applied to the direct conversion of phenols to the corresponding aryl phosphonates in one pot via reaction of phenols with SO2F2 and subsequent palladium-catalyzed cross-coupling.

Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).

NiCl 2as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide

Herein, NiCl 2is employed as a cheap precatalyst in the formation of C(sp 2)-P bond via cross-coupling reaction of phenol derivatives and phosphine oxides/phosphites. This catalytic system allows a variety of phenols with diverse functional groups to transform into phosphates with good yields. No additional additive is used in this reaction.

Synthesis of 18F-Labeled Aryl Fluorosulfates via Nucleophilic Radiofluorination

Sulfuryl fluoride gas is a key reagent for SO2F transfer. However, conventional SO2F transfer reactions have limited 18F-radiochemistry translation, due to the inaccessibility of gaseous [18F]SO2F2. Herein, we report the first SO2F2-free synthesis of aryl [18F]fluorosulfates from both phenolic and isolated aryl imidazylate precursors with cyclotron-produced 18F-. The radiochemical yields ranged from moderate to good with excellent functional group tolerance. The reliability of our approach was validated by the automated radiosynthesis of 4-acetamidophenyl [18F]fluorosulfate.

A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction

O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.

Continuous flow synthesis of aryl aldehydes by Pd-catalyzed formylation of phenol-derived aryl fluorosulfonates using syngas

This communication describes the palladium-catalyzed reductive carbonylation of aryl fluorosulfonates (ArOSO2F) using syngas as an inexpensive and sustainable source of carbon monoxide and hydrogen. The conversion of phenols to aryl fluorosulfonates can be conveniently achieved by employing the inexpensive commodity chemical sulfuryl fluoride (SO2F2) and base. The developed continuous flow formylation protocol requires relatively low loadings for palladium acetate (1.25 mol%) and ligand (2.5 mol%). Good to excellent yields of aryl aldehydes were obtained within 45 min for substrates containing electron withdrawing substituents, and 2 h for substrates containing electron donating substituents. The optimal reaction conditions were identified as 120 °C temperature and 20 bar pressure in dimethyl sulfoxide (DMSO) as solvent. DMSO was crucial in suppressing Pd black formation and enhancing reaction rate and selectivity. This journal is

A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls

A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.

Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides

A novel synthetic strategy toward N-acyl sulfamates was developed. Interestingly, fluorosulfates, a new emerging class of electrophiles, were used to construct the sulfamate core. This precludes handling of chlorosulfonyl isocyanate and sulfamoyl chloride

Nickel-catalyzed carboxylation of aryl and heteroaryl fluorosulfates using carbon dioxide

The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.

Synthesis of N-Acyl Sulfamates from Fluorosulfonates and Potassium Trimethylsilyloxyl Imidates

An efficient and operationally simple method for the synthesis of N-acyl sulfamates from fluorosulfonates and potassium trimethylsilyloxyl imidates as amide precursor is reported. This approach showed broad substrate scope, mild and base-free reaction conditions, short reaction time, and high to excellent yields. Notably, we demonstrated the power of this reaction in the rapid late-stage functionalization of three complex phenol-containing bioactive molecules. Given the prevalence of phenol-containing drugs and building blocks, this method is applicable toward a diversity-oriented drug discovery.