22233-91-6Relevant academic research and scientific papers
P-Silylation of Arenes via Organic Photoredox Catalysis: Use of p-Silylated Arenes for Exclusive o-Silylation, o-Acylation, and o-Alkylation Reactions
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Pushpendra,Mondal, Pradip Kumar
supporting information, p. 7730 - 7734 (2021/10/25)
Photocatalytic regiospecific p-silylation of arenes has been achieved by the coupling of in situ generated silyl radical with arene radical cation. The strategy involves reductive activation of PhSe-SiR3 and single electron transfer from the electron rich
Clarification on the reactivity of diaryl diselenides toward hexacyclohexyldilead under light
Hung, Vu Thai,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya,Tran, Cong Chi,Yamamoto, Yuki
, (2021/10/25)
In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6 Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy?). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
supporting information, p. 12337 - 12340 (2017/11/20)
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
A comparative study of Cu(II)-assisted vs Cu(II)-free chalcogenation on benzyl and 2°/3°-cycloalkyl moieties
Sahoo, Santosh K
, p. 2151 - 2157 (2016/01/12)
A relative synthetic strategy toward intermolecular oxidative C -Chalcogen bond formation of alkanes has been illustrated using both Cu(II) assisted vs Cu(II) free conditions. This led to construction of a comparative study of hydrocarbon benzylic and 2°/ 3°-cycloalkyl moieties bond sulfenylation and selenation protocol by the chalcogen sources, particularly sulfur and selenium, respectively. In addition, this protocol disclosed the auspicious formation of sp3 C-S coupling products over leading the sp3 C-N coupling products by using 2-mercaptobenzothiazole (MBT) substrates.
Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond
Du, Bingnan,Jin, Bo,Sun, Peipei
supporting information, p. 3032 - 3035 (2014/06/23)
A new protocol for C-S and C-Se bond formation by the direct functionalization of the C(sp3)-H bond of alkanes under metal-free conditions was developed. Using tBuOOtBu as the oxidant, the reaction of disulfides or diselenides with alkanes gave sulfides or selenides in moderate to good yields. The method was very simple and atom-economical.
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
body text, 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.
An efficient radical procedure for the halogenation and chalcogenation of B-alkylcatecholboranes
Schaffner, Arnaud-Pierre,Montermini, Florian,Pozzi, Davide,Darmency, Vincent,Scanlan, Eoin Martin,Renaud, Philippe
supporting information; experimental part, p. 1163 - 1167 (2009/06/05)
An efficient formal anti-Markovnikov addition of HX (X = Cl, Br, I, SR and SeR) to olefins under mild reaction conditionsisdes cribed. The procedure isbas ed on the hydroboration of alkeneswith catecholborane. The conversion of the intermediate B-alkylcatecholboranesto the corresponding halides, sulfides and selenides is based on a common process, i.e., generation of a radical from the alkylborane followed by abstraction of a heteroatom from an aromatic sulfonyl reagent. The efficiency of these radical reactionsis remarkable. The mildness of the reaction conditions is well illustrated by the preparation of iodoalkanes. Despite the notorious reactivity of iodoalkanes under radical reaction conditions, no product degradation wasobs erved.
Ruthenium(III) chloride catalyzed efficient synthesis of unsymmetrical diorganyl selenides via cleavage of dibenzyl and diphenyl diselenides in the presence of zinc
Zhao, Xiaodan,Yu, Zhengkun,Yan, Shenggang,Wu, Sizhong,Liu, Ren,He, Wei,Wang, Liandi
, p. 7338 - 7341 (2007/10/03)
An efficient one-pot route to unsymmetrical diorganyl selenides has been developed by ruthenium-(III) chloride catalyzed reactions of dibenzyl or diphenyl diselenides with alkyl halides in the presence of zinc. Organic iodides, bromides, and activated chlorides underwent the reactions efficiently. Unreactive organic chlorides also underwent the same type of selenation with sodium bromide as the additive.
