86211-05-4

Upstream product

• 108-98-5 thiophenol 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 824-94-2 p-methoxybenzyl chloride 
• 59664-71-0 1-((Z)-2-Chloro-2-phenylsulfanyl-vinyl)-4-methoxy-benzene 

Relevant academic research and scientific papers

Beta-lactones as antibacterial agents

The present invention relates to specific beta-lactone compounds and compositions thereof for the treatment of infections, such as, e.g., infections with bacteria or infections with protozoa, in particular infections with Gram-positive and/or Gram-negativ

Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides

(Chemical Equation Presented) A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along with the weak base, NaOAc, in anisole at 120°C. The choice of catalytic system as well as solvent turned out to be important in order to ensure a high chemoselectivity in the reaction. Both electron-rich and electron-deficient aryl bromides worked well in this reaction. Addition of 1 equiv of sodium iodide to the reaction improved the chemoselectivity with the electron-deficient aryl bromides. The thiol scope included both aryl and alkyl thiols, including 2-mercaptobenzophenones, whereby a thiocarbonylation followed by a subsequent McMurry coupling yielded differently substituted benzothiophenes. It was demonstrated that the methodology could be applied for 13C introduction into the thiophene ring.

Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides

Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.

β-lactones as privileged structures for the active-site labeling of versatile bacterial enzyme classes

(Chemical Equation Presented) A chemical proteomic strategy has been applied directly to bacterial proteomes, and b-lactones have been identified as important natural product derivatives with a high affinity to various enzyme classes (see picture). This a

A HIGHLY CONVENIENT PROCEDURE FOR THE HYDROLYSIS OF TERMINAL PHENYL VINYL SULFIDES

Terminal vinyl and chlorovinyl sulfides are hydrolyzed by 70percent perchloric acid-thiophenol in benzene to the corresponding diphenyl thioacetals and thioesters in good yields.