51558-91-9Relevant 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.
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
Tetrathiomolybdate assisted epoxide ring opening with masked thiolates and selenoates: Multistep reactions in one pot
Devan, Naduthambi,Sridhar, Perali Ramu,Prabhu, Kandikere Ramaiah,Chandrasekaran, Srinivasan
, p. 9417 - 9420 (2007/10/03)
Tetrathiomolybdate provides an easy access to β-hydroxy disulfides, β-hydroxy sulfides, and selenides from epoxides in a tandem, multistep process in one pot. This strategy has been utilized effectively in the construction of thiabicylo[3.2.2]nonane derivative 24.
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.
TRANS 1,2-FUNCTIONALIZATION OF CYCLOALKENES USING SELENIUM INTERMEDIATES
Ceccherelli, P.,Curini, M.,Marcotullio, M. C.,Rosati, O.
, p. 3175 - 3178 (2007/10/02)
The reaction of excess phenylselenenyl halides with trisubstituted cyclic olefins in aqueous acetonitrile is regio- and stereospecific and affords trans halohydrins in excellent yields.The reaction proceeds through the formation of a β-hydroxyalkyl phenyl selenide which evolves to halohydrin presumably via an epoxy-intermediate.
N-PHENYLSELENOPHTHALIMIDE (NPSP) A VALUABLE SELENENYLATING AGENT
Nicolaou, K. C.,Petasis, N. A.,Claremon, D. A.
, p. 4835 - 4842 (2007/10/02)
The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality.Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.D
PHENYLSELENENYL CHLORIDE IN ACETONITRILE-WATER; A HIGHLY CONVENIENT REAGENT FOR HYDROXYSELENATION OF OLEFINS AND PREPARATION OF CYCLIC ETHERS FROM DIENES
Toshimitsu, Akio,Aoai, Toshiaki,Owada, Hiroto,Uemura, Sakae,Okano, Masaya
, p. 5301 - 5306 (2007/10/02)
The reaction of phenylselenenyl chloride with olefins in aqueous acetonitrile affords β-hydroxyalkyl phenyl selenides in excellent yields, providing the most convenient method for hydroxyselenation of olefins so far reported.When the reaction was applied to conjugated dienes, monohydroxyselenated products were obtained in good to excellent yields.From non-conjugated dienes, on the other hand, cyclic ethers containing two phenylseleno groups were produced in good to excellent yields, the first step of this reaction being the hydroxyselenation of one double bond.
Highly Convenient Method for Hydroxyselenation of Olefins
Toshimitsu, Akio,Aoai, Toshiaki,Owada, Hiroto,Uemura, Sakae,Okano, Masaya
, p. 412 - 413 (2007/10/02)
Reaction of phenylselenenyl chloride with olefins in aqueous acetonitrile affords β-hydroxyselenides (2) in excellent yields, providing a most convenient method for the hydroxyselenation of olefins.
