37773-41-4

Upstream product

• 74-96-4 ethyl bromide 
• 1694-07-1 4-methoxyphenyl methyl selenide 
• 75-03-6 ethyl iodide 
• 628-39-7 diethyl diselenide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 

Relevant academic research and scientific papers

An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions

An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bio

Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

An atom-economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.

Synthesis and characterization of alkyl aryl selenides from arylselenomagnesium halides

Arylselenomagnesium halides, ArSeMgX, obtained by the reaction of elemental selenium with arylmagnesium halides, react with alkyl halides to afford alkyl aryl selenides in good yields.This constitutes a relatively simpler and convenient method for the preparation of a number of unsymmetrical selenides.The compounds prepared have been characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectral studies.

Nucleophilic Aromatic Substitutions of Unactivated Aryl Halides by Methyl Selenide Anions. Synthesis and Selective Dealkylations of Aryl Alkyl Selenides

Lithium methyl selenide, easily prepared from powdered gray selenium and MeLi, reacts with unactivated aryl halides, in DMF, to afford the aryl methyl selenides as a result of a nucleophilic aromatic substitution.The aryl methyl selenides are rapidly dealkylated in the reaction medium by MeSeLi to give the aryl selenide anions.Addition of an alkyl halide or of cyanogen iodide gives rise to the formation of aryl alkyl selenides or aryl selenocyanates in good yields.From competitive experiments, carried out on compounds of the type ArClSeR and ArClSR, it has been shown that an RSe group is as efficient as an RS group in activating the nucleophilic aromatic substitution of a chlorine atom by MeS or MeSe anions in DMF. (Alkylthio)phenyl and alkoxyphenyl alkyl selenides can be selectively dealkylated by nucleophilic aliphatic substitution with MeSNa or MeSeLi in DMF or by electron transfer with sodium in HMPA.In the first case the easiness with which the dealkylation occurs follows the order ArSeMe > ArOMe > ArSMe, whereas in the second case the order is ArSeR > ArSR > ArOR.The synthetic utility of these reactions is exemplified and discussed.