39192-26-2Relevant academic research and scientific papers
Reactive separation of β-bromoethylbenzene from α-β-bromoethylbenzene mixtures: a Zn2+-mediated radical polymerization mechanism
Deng, Tianyu,Tian, Jiaming,Yan, Binhang,Zhu, Junqiu
, p. 1219 - 1222 (2022/02/03)
A Zn2+-induced reactive separation method for the purification of β-bromoethylbenzene from α-β-bromoethylbenzene mixtures is discovered, where the selective decomposition of α-bromoethylbenzene follows a radical mechanism. Zn2+ facilitates the homolysis of the C-Br bond of halohydrocarbons with benzyl bromide, enabling the separation of the corresponding isomers with almost identical physical properties.
Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
, p. 13029 - 13032 (2020/11/07)
A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes
Badsara, Satpal Singh,Liu, Yi-Chen,Hsieh, Ping-An,Zeng, Jing-Wen,Lu, Shao-Yi,Liu, Yi-Wei,Lee, Chin-Fa
supporting information, p. 11374 - 11377 (2014/11/08)
A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.
Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
Banerjee, Subhash,Adak, Laksmikanta,Ranu, Brindaban C.
supporting information; experimental part, p. 2149 - 2152 (2012/05/05)
A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.
Chemoenzymatic approaches to obtain chiral-centered selenium compounds
Brondani, Patricia B.,Guilmoto, Nathalie M. A. F.,Andrade, Leandro H.,Dudek, Hanna M.,Fraaije, Marco W.
, p. 10431 - 10436,6 (2012/12/12)
The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved.
Chemoenzymatic approaches to obtain chiral-centered selenium compounds
Brondani, Patrícia B.,Guilmoto, Nathalie M.A.F.,Dudek, Hanna M.,Fraaije, Marco W.,Andrade, Leandro H.
, p. 10431 - 10436 (2013/01/15)
The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved.
A novel regioselective reaction of styrene with magnesium organoselenolates to afford unsymmetrical selenides catalyzed by CuI and l-proline
Gao, Fei,Tang, Yu,Li, Zhi-Hao,Pan, Feng,Yang, Jun,Zhang, Yuan-Ming
supporting information, p. 5688 - 5690 (2012/10/29)
A novel regioselective reaction of styrene with the prepared magnesium organoselenolates from magnesium, alkyl or aryl bromides, and selenium has been developed in one pot. The reaction catalyzed by CuI and l-proline proceeded in THF, water, and toluene. The scope and limitations of this reaction have been examined. The reaction afforded unsymmetrical selenides containing 12 new compounds in good to high yields.
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.
On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
Peppe, Clovis,Borges De Castro, Lierson
experimental part, p. 678 - 683 (2009/10/30)
The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better organyl halides capable to produce stable carbocations.
Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters
Ranu, Brindaban C.,Mandal, Tanmay
, p. 5793 - 5795 (2007/10/03)
Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.
