Silver-Catalyzed One-Pot Three-Component Selective Synthesis of β-Hydroxy Selenides
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.).
Copper-Catalyzed Oxirane-Opening Reaction with Aryl Iodides and Se Powder
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.
Ultrasound assisted ring-opening reaction of epoxides with 1,2-diphenyldiselenide
Ultrasound assisted ring-opening of epoxides with 1,2-diphenyldiselenide in PEG-400/H2O in the presence of sodium dithionite has been developed, affording β-hydroxy selenides with high regioselectivity in good to excellent yields. Importantly,
Cheng, Tianxing,Zheng, Xiangyong,Ke, Qiang
experimental part
p. 522 - 524
(2011/11/30)
Rongalite-promoted odourless and highly regioselective synthesis of β-hydroxyselenides under solvent-free conditions
An efficient and facile procedure for the odourless and highly regioselective synthesis of β-hydroxyselenides by the ring-opening of epoxides with 1,2-diphenyldiselenide in the presence of Rongalite and K2CO3 under solven
Regioselective ring-opening reactions of 1,2-epoxides with thiols and arylselenols directly promoted by [Bmim]BF4
Regioselective ring-opening reactions of 1,2-epoxides with ArSH and ArSeH promoted by ionic liquid [Bmim]BF4 were investigated. A variety of β-hydroxy selenides and β-hydroxy sulfides were obtained in excellent yields (81-99%) with good regiose
Yang, Ming-Hua,Yan, Guo-Bing,Zheng, Yun-Fa
supporting information; experimental part
p. 6471 - 6474
(2009/04/06)
EXCHANGE REACTIONS IN OLEFIN OXIDE-PHENYL β-HYDROXYALKYL SELENIDE SYSTEM
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Malievskii, A. D.,Gorbunova, O. I.
p. 2504 - 2505
(2007/10/02)
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