21113-89-3Relevant articles and documents
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
, 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.
Silver-Catalyzed One-Pot Three-Component Selective Synthesis of β-Hydroxy Selenides
Leng, Tao,Wu, Ge,Zhou, Yun-Bing,Gao, Wenxia,Ding, Jinchang,Huang, Xiaobo,Liu, Miaochang,Wu, Huayue
supporting information, p. 4336 - 4340 (2018/10/15)
A convenient, multi-component reaction of organoboronic acids, selenium powder and epoxides has been developed, providing an efficient protocol for the synthesis of β-hydroxy selenides with excellent selectivity and good functional group tolerance. Preliminary mechanistic studies suggest that the reaction proceeds through the silver-catalyzed radical selenation of the arylboronic acids to generate a diselenide, and subsequent selenium-mediated selective ring-opening arylselenation of epoxides. (Figure presented.).
Preparation method of beta-hydroxyphenyl selenide compound
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Paragraph 0140; 0141; 0142; 0143; 0144; 0145; 0146-0148, (2017/12/27)
The invention relates to the technical field of synthesis of organic compounds and particularly relates to a preparation method of a beta-hydroxyphenyl selenide compound. The preparation method comprises the step of with aryl boronic acid with a structure presented by a formula (I), elemental selenium and an ethylene oxide derivative presented by a formula (II) as the raw materials, and carrying out insertion reaction on elemental selenium in a reaction solvent under the common effect of a copper catalyst, silver salt and alkali, so as to obtain the beta-hydroxyphenyl selenide compound represented by a formula (III), wherein R1 and R2 are respectively independently selected from one of H, a benzene ring, a naphthalene ring, a heterocyclic ring, a substituted benzene ring, linear alkyl, branched chain, halogen, nitryl and a cyano group.
Copper-Catalyzed Oxirane-Opening Reaction with Aryl Iodides and Se Powder
Min, Lin,Wu, Ge,Liu, Miaochang,Gao, Wenxia,Ding, Jinchang,Chen, Jiuxi,Huang, Xiaobo,Wu, Huayue
, p. 7584 - 7590 (2016/09/09)
Using Se powder as the selenating reagent, the copper-catalyzed double C-Se cross-coupling of aryl iodides, epoxides, and elemental selenium has been developed. This strategy provides a straightforward approach to the synthesis of β-hydroxy phenylselenides with excellent regioselectivity of the ring opening reaction. This process proceeds in generally good yields and is compatible with a broad range of functional groups.
Lipase-catalyzed resolution of β-hydroxy selenides
Gruttadauria, Michelangelo,Meo, Paolo Lo,Riela, Serena,D'Anna, Francesca,Noto, Renato
, p. 2713 - 2721 (2007/10/03)
Eleven β-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 °C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic β-hydroxy selenides is also discussed. Enantiopure β-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure β-hydroxy selenide.
The reaction of the a-selenium stabilized copper reagents ArSeCH2Cu(CN)ZnCl
Duan, Aldehydesf De-Hui,Huang, Xian
, p. 26 - 27 (2007/10/03)
a-Arylseleno-substituted zinc and copper organometallics, in the presence of a Lewis acid, can react with aldehydes, ketones and enals with high chemoselectivity and_regioselectivity.
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.
