69562-10-3Relevant articles and documents
Solvent-controlled halo-selective selenylation of aryl halides catalyzed by Cu(II) supported on Al2O3. A general protocol for the synthesis of unsymmetrical organo mono- and bis-selenides
Chatterjee, Tanmay,Ranu, Brindaban C.
, p. 7145 - 7153 (2013/08/23)
Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl-alkyl, aryl-heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another diaryl/diheteroaryl/dialkyl diselenide in PEG-600 in the second step produces unsymmetrical diaryl, diheteroaryl, or aryl-alkyl bis-selanyl benzene. A library of functionalized organo mono- and bis-selenides, including a potent biologically active molecule and a couple of analogues of bioactive selenides, were obtained in high yields by this protocol. The reactions are chemoselective and high yielding. The Cu-Al2O 3 catalyst is recycled for seven runs without any appreciable loss of activity.
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.
Iridium-catalyzed allylic alkylations of sodium phenyl selenide
Cui, Ruimin,Guo, Xinwen,Zheng, Shengcai,Zhao, Xiaoming
, p. 2647 - 2651 (2013/01/15)
An iridium-catalyzed allylic substitution of sodium phenyl selenide with unsymmetrical allyl carbonates was accomplished, which produced the linear allyl phenyl selenides in 38%-74% yields. An asymmetric iridium-catalyzed allylation of sodium phenyl selen
Ruthenium(iii)-catalysed phenylselenylation of allyl acetates by diphenyl diselenide and indium(i) bromide in neat: Isolation and identification of intermediate
Saha, Amit,Ranu, Brindaban C.
experimental part, p. 1763 - 1767 (2011/04/26)
A fast and efficient phenylselenylation of allyl acetates by diphenyl diselenide and indium(i) bromide has been achieved in neat under the catalysis of Ru(acac)3. The intermediate complex of diphenyl diselenide and indium has been isolated and identified as a polymeric pentacoordinated In(iii) selenolate complex, [In(SePh)3]n.
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.
1-(organoselanyl)perfluoroalkanols: A stable and efficient precursor for organoselenols
Yamamoto, Terahisa,Moriura, Eri,Sawa, Arisa,Yoshimatsu, Mitsuhiro
scheme or table, p. 1046 - 1047 (2009/12/03)
The 1-(organoselanyl)perfluoroalkanols 1, 3, 4, and 10 were successfully prepared and reactions with hexanoyl chlorides to produce the corresponding esters 5, 7, and 8, accompanied by the selenoesters 6 were conducted. The DBU-mediated alkylations of the heptafluorobutanols 4, 10, and the α-p-nitro-benzoate 2 with alkyl halides easily provided alkyl phenyl selenides 9a-9i and 11a-11c in good to high yields. Copyright
Synthesis of allyl selenides by palladium-catalyzed decarboxylative coupling
Waetzig, Shelli R.,Tunge, Jon A.
supporting information; experimental part, p. 3311 - 3313 (2009/02/04)
This communication details the Pd-catalyzed decarboxylation of selenocarbonates; use of a chiral nonracemic catalyst affords enantioenriched allyl selenides which undergo stereospecific [2,3]-sigmatropic rearrangements to form enantioenriched allylic amines and chlorides. The Royal Society of Chemistry.
Employment of palladium pincer-complexes in phenylselenylation of organohalides
Wallner, Olov A.,Szabo, Kalman J.
, p. 9215 - 9221 (2007/10/03)
Palladium pincer-complex-catalyzed selenylation of propargyl-, allyl-, benzyl-, and benzoyl halides could be achieved under mild reaction conditions employing trimethylstannylphenylselenide as selenylating agent. This reaction has a high functional group
A Facile Method for Synthesis of Alkyl Phenyl Selenides. The Reaction of Diphenyl Diselenide with Oxygen-containing Compounds Using La/Me 3SiCl/cat.I2/cat.CuI System
Nishino, Toshiki,Nishiyama, Yutaka,Sonoda, Noboru
, p. 918 - 919 (2007/10/03)
Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me 3SiCl/cat.I2/cat.CuI. It was suggested that alkyl phenyl sele
A novel synthesis of allyl and propargyl selenides promoted by indium
Zheng,Bao,Zhang
, p. 79 - 83 (2007/10/03)
Promoted by indium, allylic and propargyl bromides react with diorganyl diselenides in THF to give allylic and propargyl selenides in moderate to good yields.
