35446-84-5Relevant academic research and scientific papers
Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins
Liang, Zhi-Peng,Yi, Wei,Wang, Peng-Fei,Liu, Gong-Qing,Ling, Yong
, p. 5292 - 5304 (2021/04/06)
A three-component reaction of olefin, diselenide and water, alcohols, phenol, carboxylic acid, or amine by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provides access to a wide range of vicinally functionalized selenoderivatives under ambient conditions with mostly excellent yields and high diastereoselectivity. The developed reaction displays high levels of functional group compatibility and is suitable for the late-stage functionalization of styrene-functionalized biomolecules. Preliminary investigations on the mechanism of the reaction are also presented.
Synthesis of β-hydroxy aryl selenides via transition-metal-free three-component reaction of arylamines, elemental selenium, and epoxides
Wang, Hongwei,Li, Hongchen,Bai, Yalong,Hei, Yanling,Chen, Junwei,Yu, Guoqi,Zhou, Yun-Bing
supporting information, p. 3621 - 3629 (2021/06/21)
An efficient protocol for the construction of valuable β-hydroxy aryl selenides from easily available arylamines, elemental selenium, and epoxides through a transition-metal-free radical process is described. A wide variety of β-hydroxy aryl selenides were obtained in good to excellent yields with excellent stereo- and regioselectivity. In this reaction, two C-Se bonds can be built along with the cleavage of a C-N and C-O bond, demonstrating the high step economy and efficiency of this approach.
New Catalytic Method for the Synthesis of β-Hydroxy Selenides
Zhang, Yikun,Wu, Sixue,Yan, Jie
, p. 654 - 658 (2016/08/24)
In the presence of NH4I as catalyst and m-chloroperbenzoic acid as oxidant, the Se–Se bond cleavage of diselenides undergoes smoothly. The in?situ generated reactive electrophilic Se species reacts with alkenes quickly, and a series of β-hydroxy selenides are prepared in good yields. This new catalytic method for synthesis of β-hydroxy selenides is a stereospecific anti addition, which occurs with a Markovnikov orientation.
Syntheses of the optically active terpene hydroxyphenylselenides
Scianowski, Jacek,WeLniak, MirosLaw
experimental part, p. 1440 - 1447 (2010/03/24)
The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.
Preparation of the first bench-stable phenyl selenolate: An interesting "on water" nucleophilic reagent
Santi, Claudio,Santoro, Stefano,Battistelli, Benedetta,Testaferri, Lorenzo,Tiecco, Marcello
scheme or table, p. 5387 - 5390 (2009/05/07)
In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring ope
A simple zinc-mediated preparation of selenols
Santi, Claudio,Santoro, Stefano,Testaferri, Lorenzo,Marcello Tiecco
scheme or table, p. 1471 - 1474 (2009/04/07)
Under acidic conditions zinc reduces diselenides to afford selenols, which can be either isolated or treated in situ with alkyl halides to produce alkyl selenides or with epoxides to give β-hydroxyselenides. Georg Thieme Verlag Stuttgart.
Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes
Piovan, Leandro,Capelari, Marina,Andrade, Leandro H.,Comasseto, Joao V.,Porto, Andre L.M.
, p. 1398 - 1402 (2008/02/11)
An efficient synthesis of the chiral cyclic secondary alcohols, trans-2-(phenylseleno)cyclohexanol 1a and cis-2-(phenylseleno)cyclohexanol 1a, was obtained by enzymatic reduction of 2-(phenylseleno)cyclohexanone 1 using whole fungal cells. Five strains of white-rot basidiomycetes were examined; Irpex lacteus CCB 196, Pycnoporus sanguineus CCB 196, Trametes rigida CCB 285, Trametes versicolor CCB 202 and Trichaptum byssogenum CCB 203. Cells of T. rigida CCB 285 gave alcohols cis-(RS)-1a and trans-(SS)-1a in high enantiomeric excesses (ca. 99%).
Synthesis of β-hydroxy selenides using benzeneselenol and oxiranes under supramolecular catalysis in the presence of β-cyclodextrin in water
Sridhar,Srinivas,Surendra,Krishnaveni, N. Srilakshmi,Rao, K. Rama
, p. 8837 - 8839 (2007/10/03)
A simple and efficient method for the synthesis of β-hydroxy selenides is reported at room temperature in impressive yields for the first time by the highly the regioselective ring-opening of oxiranes with benzeneselenol in water under supramolecular cata
Vertical and nonvertical participation by sulfur, selenium, and tellurium
White, Jonathan M.,Lambert, Joseph B.,Spiniello, Marisa,Jones, Scott A.,Gable, Robert W.
, p. 2799 - 2811 (2007/10/03)
The mechanism of stabilization of positive charge on carbon by sulfur, selenium, or tellurium at the: β-position has been investigated kinetically, by measurement of rate enhancements, and structurally, by variation of the bond strength to the leaving group. Stabilization can occur either nonvertically with formation of a bridged intermediate or vertically through hyperconjugation within an open carbocation. We observed large rate enhancements (105 for S, 106 for Se) in 97% aqueous trifluoroethanol with trifluoroacetate as the leaving group. These enhancements are consistent with either mechanism. Product structures also are consistent with either mechanism. Nine crystal structures revealed that the bond to the leaving group (C-O) is lengthened by the presence of S or Se at the β-position, in proportion to the basicity of the leaving group. This lengthening is not accompanied by angle distortions expected for the bridging mechanism. The crystallographic data support vertical (hyperconjugative) character along the reaction coordinate, more so for selenium than sulfur.
Oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). A new method for the electrophilic phenylselenenylation of alkenes under mild conditions
Tiecco,Testaferri,Temperini,Bagnoli,Marini,Santi
, p. 1767 - 1771 (2007/10/03)
The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.
