203247-48-7

Upstream product

• 106-53-6 para-bromobenzenethiol 
• 292638-85-8 acrylic acid methyl ester 
• 2935-90-2 Methyl 3-mercaptopropionate 
• 34176-08-4 sodium 4-bromobenzenesulfinate 

Relevant academic research and scientific papers

Direct biocatalysed synthesis of first sulfur-, selenium- and tellurium- containing l-ascorbyl hybrid derivatives with radical trapping and GPx-like properties

6-O-l-Ascorbyl selenoesters, thioesters and telluroesters can be efficiently and directly prepared from l-ascorbic acid and suitable functionalised chalcogenoesters through lipase-catalysed transesterification reactions. Novel synthesised l-ascorbyl deriv

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

Synthesis of Highly Enantioenriched Sulfonimidoyl Fluorides and Sulfonimidamides by Stereospecific Sulfur–Fluorine Exchange (SuFEx) Reaction

Sulfonimidamides present exciting opportunities as chiral isosteres of sulfonamides, with potential for additional directional interactions. Here, we present the first modular enantioselective synthesis of sulfonimidamides, including the first stereoselective synthesis of enantioenriched sulfonimidoyl fluorides, and studies on their reactivity. A new route to sulfonimidoyl fluorides is presented from solid bench-stable, N-Boc-sulfinamide (Boc=tert-butyloxycarbonyl) salt building blocks. Enantioenriched arylsulfonimidoyl fluorides are shown to be readily racemised by fluoride ions. Conditions are developed, which trap fluoride and enable the stereospecific reaction of sulfonimidoyl fluorides with primary and secondary amines (100 % es, es=enantiospecificity) generating sulfonimidamides with up to 99 % ee. Aryl and alkyl sulfonimidoyl fluoride reagents are suitable for mild late stage functionalisation reactions, exemplified by coupling with a selection of complex amines in marketed drugs.

Microwave-Assisted Pd-Catalyzed Desulfitative C-S Coupling of Arylsulfinate Metal Salts and Alkanethiols

This paper reports a palladium-catalyzed C-S coupling of arylsulfinate metal salts and alkanethiols via liberation of sulfur dioxide. The use of PdCl2 as the catalyst in combination with AgNO3 as the oxidant under microwave irradiation results in the synthetically and biologically important aryl alkyl sulfides. A variety of arylsulfinate metal salts, such as sodium, potassium, lithium, silver, zinc, and copper salts, are tolerated well in this reaction.

Squaric acid as an impressive organocatalyst for Michael addition in water

A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.

"On-water" conjugate additions of anilines

The conjugate addition of anilines onto unsaturated ketones, esters and N-acylpyrroles was investigated. Based on a recently proposed explanation for the phenomenon of on-water catalysis, operationally simple and mild reaction conditions for effecting these addition reactions have been developed. The success of these additions provides further support for the acid-catalysed nature of on-water chemistry.