76529-36-7Relevant academic research and scientific papers
Atom efficient preparation of zinc selenates for the synthesis of selenol esters under “On Water” conditions
Sancineto, Luca,Vargas, Jaqueline Pinto,Monti, Bonifacio,Arca, Massimiliano,Lippolis, Vito,Perin, Gelson,Lenardao, Eder Joao,Santi, Claudio
, (2017/06/29)
We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic acyl chlorides and tolerates the presence of other functionalities in the starting material.
General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis
Temperini, Andrea,Piazzolla, Francesca,Minuti, Lucio,Curini, Massimo,Siciliano, Carlo
, p. 4588 - 4603 (2017/05/12)
A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.
Reaction of Acyl Chlorides with in Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran
Bellino, Gemma,Scisciani, Marialaura,Vargas, Jaqueline Pinto,Sancineto, Luca,Bagnoli, Luana,Marini, Francesca,Lüdtke, Diogo Seibert,Lenardao, Eder Joao,Santi, Claudio
, (2016/07/28)
Attempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to
Syntheses of selenoesters through C-H selenation of aldehydes with diselenides under metal-free and solvent-free conditions
Liou, Jyun-Cyuan,Badsara, Satpal Singh,Huang, Yu-Ting,Lee, Chin-Fa
, p. 41237 - 41244 (2014/12/10)
A DTBP-promoted C-H selenation of aldehydes with diselenides under metal-free and solvent-free conditions is described. This system shows good functional group compatibility, functional groups including bromo, trifluoromethyl, chloro, amine and heterocycle-containing moieties including thiophene and furan are all tolerated by the reaction conditions employed. Both diaryl and dialkyl diselenides reacted smoothly with aldehydes to provide selenoesters in good to excellent yields. This journal is
Syntheses of selenoesters through C-H selenation of aldehydes with diselenides under metal-free and solvent-free conditions
Liou, Jyun-Cyuan,Badsara, Satpal Singh,Huang, Yu-Ting,Lee, Chin-Fa
, p. 41237 - 41244 (2015/05/20)
A DTBP-promoted C-H selenation of aldehydes with diselenides under metal-free and solvent-free conditions is described. This system shows good functional group compatibility, functional groups including bromo, trifluoromethyl, chloro, amine and heterocycle-containing moieties including thiophene and furan are all tolerated by the reaction conditions employed. Both diaryl and dialkyl diselenides reacted smoothly with aldehydes to provide selenoesters in good to excellent yields. This journal is
On water preparation of phenylselenoesters
Santi, Claudio,Battistelli, Benedetta,Testaferri, Lorenzo,Tiecco, Marcello
supporting information; experimental part, p. 1277 - 1280 (2012/06/04)
PhSeZn-halides react under "on water" mild conditions with acid chlorides to provide a high yield route to a variety of aromatic and aliphatic phenylselenoesters.
A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite
Dan, Weixing,Deng, Hongjuan,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
experimental part, p. 7384 - 7388 (2010/10/02)
Rongalite promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions.
Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters
Munbunjong, Wanida,Lee, Eun Hwa,Ngernmaneerat, Poonlarp,Kim, Sung Jun,Singh, Gurpinder,Chavasiri, Warinthorn,Jang, Doo Ok
experimental part, p. 2467 - 2471 (2009/08/15)
A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.
Synthesis of selenol esters: Palladium-catalyzed coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide
Nishiyama, Yutaka,Tokunaga, Keiji,Kawamatsu, Hiroaki,Sonoda, Noboru
, p. 1507 - 1509 (2007/10/03)
It was found that palladium complex catalyzed three-component coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide to afford the corresponding selenol esters in moderate to good yields.
Oxidation of Hydrazines with Benzeneseleninic Acid and Anhydride
Back, Thomas G.,Collins, Scott,Ker, Russell G.
, p. 1564 - 1570 (2007/10/02)
Benzeneseleninic acid (1) and anhydride (2) oxidize hydrazine or 1,2-disubstituted derivatives to corresponding diazenes.Hydrazides afford selenoesters 4, N,N'-diacyl- or diaroylhydrazines 5, and carboxylic acids.Benzeneselenenic acid (7) is a required intermediate in selenoester formation and may be generated independently by the reaction of triphenylphosphine with 1.Selenoesters are efficiently prepared by the slow addition of a mixture of the hydrazide and triphenylphosphine to 1 in dichloromethane solution.Polar solvents are unsuitable.Inverse addition provides compounds 5 as major products.Oxidation of hydrazides of structure HO-(CH2)nCONHNH2 gives the corresponding selenoesters 14 and acids 16 when n=11 or 14 lactones 17 and 18 when n=4 or 3.Arylhydrazines react with 1 or 2 to furnish arenes 23 and aryl phenyl selenides 24.
