60718-41-4Relevant academic research and scientific papers
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.
Acylation of diselenides and disulfides with N-acylbenzotriazoles promoted by SmI2
Tu, Ya Wei,Zhou, Lie Jin,Lv, Xin,Wang, Xiao Xia
, p. 435 - 439 (2014/05/06)
The acylation of diselenides or disulfides with N-acylbenzotriazoles mediated by SmI2 has been achieved successfully without the presence of HMPA, and the corresponding selenolesters or thioesters have been prepared in good yields.
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.
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.
Palladium-catalyzed selenoacylation of allenes leading to the regioselective formation of functionalized allyl selenides
Toyofuku, Masashi,Murase, Erika,Fujiwara, Shin-ichi,Shin-ike, Tsutomu,Kuniyasu, Hitoshi,Kambe, Nobuaki
supporting information; experimental part, p. 3957 - 3960 (2009/05/30)
(Chemical Equation Presented) Palladium-catalyzed regio- and stereoselective selenoacylation of allenes with selenol esters proceeded to produce functionalized allyl selenides with the acyl moiety at the inner carbon and the SePh group at the terminal car
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.
A one-pot conversion of carboxylic acids into homoallylic alcohols
Ollivier,Panchaud,Renaud
, p. 1573 - 1578 (2007/10/03)
A one-pot procedure for the conversion of carboxylic acids into homoallylic alcohols under remarkably mild and selective conditions is described. The triethylammonium salts of alkanoic acids are treated with Bu3P/PhSeCl to afford the correspond
Acyl Radicals: Intermolecular and Intramolecular Alkene Addition Reactions
Boger, Dale L.,Mathvink, Robert J.
, p. 1429 - 1443 (2007/10/02)
A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed.Primary alkyl-, vinyl-, and arylsubstituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction.Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally >/= 1 x 106 s-1 with some occuring at rates >/= 3 x 107 s-1.Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical conditions.Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.
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.
