18168-86-0

Upstream product

• 20828-73-3 methylsulfanylium 
• 634-36-6 1,2,3-trimethoxybenzene 
• 624-92-0 Dimethyldisulphide 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 150563-50-1 2,6-dimethoxy-4-thiocyanatophenol 
• 74-88-4 methyl iodide 

Downstream Products

• 38417-51-5 5-Methanesulfinyl-1,2,3-trimethoxy-benzene 
• 16807-30-0 3,4,5-trimethoxyphenylmercaptan 
• 1885-35-4 3,4,5-trimethoxybenzonitrile 
• 100-68-5 methyl-phenyl-thioether 

Relevant academic research and scientific papers

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction

We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.

Electrochemically generated organothiating reagents and their use

Electrolysis of organic disulfides in liquid sulfur dioxide is used to obtain organothiating agents, which can then be reacted with appropriate substrates to effect the synthesis of organothioaromatic compounds efficiently and in high yields. With appropriate phenolic compounds, regioselective substitution occurs in which para substitution greatly exceeds ortho substitution.

Electrochemical electrophilic aromatic methylthiation in liquid SO2

Controlled potential electrolysis of dimethyldisulfide in liquid sulfur dioxide provides a strongly electrophilic methylthiating agent. This species methylthiates strongly to weakly activated arenes in good to excellent yield.

Electrophilic substitutions with the electrogenerated sulfenium cation R1-S+

The sulfenium cation R1-S+ electrogenerated by oxidation of organic disulfides, reacts with phenols, aromatic ethers and ketones bearing an hydrogen atom in α position, to give alkyl (aryl) sulfanyl compounds.