- Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins
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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.
- Liang, Zhi-Peng,Yi, Wei,Wang, Peng-Fei,Liu, Gong-Qing,Ling, Yong
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p. 5292 - 5304
(2021/04/06)
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- New elements on the behaviour of a bissulfinylmethyl radical
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In this article, we have studied the generation of a bissulfinylmethyl radical from the corresponding TEMPO and phenylselenyl bissulfoxide precursors. No univocal formation of the bissulfinylmethyl radical has been observed. Instead, complex mixtures have been obtained in thermal or photochemical conditions, showing prominent C-S homolytic bond cleavage.
- Mallorquin, Rocio Martinez,Vincent, Guillaume,Derat, Etienne,Malacria, Max,Goddard, Jean-Philippe,Fensterbank, Louis
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p. 346 - 353
(2013/05/09)
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- Ultrasound assisted ring-opening reaction of epoxides with 1,2-diphenyldiselenide
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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
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experimental part
p. 522 - 524
(2011/11/30)
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- Rongalite-promoted odourless and highly regioselective synthesis of β-hydroxyselenides under solvent-free conditions
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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
- Lv, Guangshu,Li, Ting,Hu, Ruijia,Chen, Jiuxi,Ding, Jinchang,Wu, Huayue
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experimental part
p. 549 - 552
(2011/02/22)
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- Active metallic indium-mediated ring-opening of epoxides with diphenyl diselenides: A novel one-pot synthesis of β-hydroxy selenides in aqueous media
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An efficient and simple one-pot procedure for the synthesis of β-hydroxy selenides in aqueous media through highly regioselective ring-opening of epoxides with diphenyl diselenide in the presence of active metallic indium is described.
- Chen, Xian,Wu, Huayue,Su, Weike,Xu, Rong,Liu, Miaochang,Ding, Jinchang
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p. 325 - 327
(2008/02/12)
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- Stereo- and regioselective zinc-mediated ring-opening of epoxides with diselenides
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Two convenient rapid, efficient, stereoselective and highly regioselective methods for the synthesis of β-hydroxy selenides by the direct opening of epoxides with diselenides in acetonitrile in the presence of either Zn/AlCl 3 or zinc powder in
- Movassagh, Barahman,Shamsipoor, Mojgan
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p. 1316 - 1318
(2007/10/03)
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- A novel role of zeolite NaY in the thermal reaction of alkyl aryl selenoxides in its supercages
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Thermal reaction of alkyl aryl selenoxides in the presence of water or methanol in the supercage of zeolite NaY gave β-hydroxy- or β-methoxyalkyl aryl selenides, respectively, and NaY played a novel role to stabilize reactive ArSeOH and to separate an anion of -OH from a carbonium ion which was simultaneously present with the -OH in a supercage.
- Zhang, Wanxuan,Yu, Haitao,Gao, Yu,Meng, Jiben,Matsuura, Teruo
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p. 498 - 499
(2007/10/03)
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- The reaction of the a-selenium stabilized copper reagents ArSeCH2Cu(CN)ZnCl
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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.
- Duan, Aldehydesf De-Hui,Huang, Xian
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- Iodosobenzene diacetate and diphenyl diselenide: An electrophilic selenenylating agent of double bonds
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Phenylseleno-acetoxylation, hydroxylation, etherification and lactonization products are obtained in good yields from the reaction of alkenes with diphenyl diselenide and iodosobenzene diacetate, in acetonitrile.
- Tingoli, Marco,Tiecco, Marcello,Testaferri, Lorenzo,Temperini, Andrea
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p. 1769 - 1778
(2007/10/03)
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- Activation of Sn-Se bond: Regioselective ring opening reaction of epoxides with tributylstannyl phenylselenolate in the presence of a Lewis acid
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When tributylstannyl phenylselenolate (Bu3SnSePh) was allowed to react with epoxides in the presence of BF3·OEt2 as a Lewis acid, the ring opening reaction of epoxides proceeded with complete regioselectivity to afford the
- Nishiyama, Yutaka,Ohashi, Hironori,Itoh, Kazuyoshi,Sonoda, Noboru
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p. 159 - 160
(2007/10/03)
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- Oxidative Cleavage of Diselenide by m-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
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Diphenyl diselenide was found to be readily converted into benzeneselenenyl-m-nitrobenzenesulfonate (PhSeOSO2C6H4NO2-m) by treating with m-nitrobenzenesulfonyl peroxide.When the selenenyl sulfonate thus formed was allowed to react in situ with olefins, such as cyclohexene, 1-octene, or styrene, in the presence of various nucleophiles, the adducts of benzeneselenenyl group and a nucleophile were obtained.As the nucleophiles water, methanol, acetic acid, phenol, and anisole could be employed; oxyselenenylated : R=H, Me, Ac, and Ph) and arylselenenylated : R=H and Me) adducts were afforded.Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene.Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were similarly performed by the selenenyl sulfonate to afford corresponding benzeneselenenylated cyclic ethers and lactones.The selenenyl sulfonate was also found to be a highly reactive benzeneselenenylating reagent for aromatic rings, such as anisole, phenol, acetanilide, toluene, and benzene.
- Yoshida, Masato,Sasage, Shuichi,Kawamura, Kyoko,Suzuki, Takashi,Kamigata, Nobumasa
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p. 416 - 422
(2007/10/02)
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- UNUSUAL REACTIVITY OF SELENOBORANES TOWARDS EPOXIDES: NEW SELECTIVE ROUTES TO β-HYDROXYSELENIDES AND ALLYLALCOHOLS
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Selenoboranes react with terminal, α, β- di- and trisubstituted epoxides to produce β-hydroxyselenides (or olefins) in the two first cases and allyl alcohols in the last one.A very high stereodescrimination has been observed for α,β-disubstituted epoxides: the cis epoxide being much more reactive.
- Cravador, A.,Krief, A.
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p. 2491 - 2494
(2007/10/02)
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- REGIOSELECTIVE AND CONNECTIVE ROUTES TO OXETANES AND TETRAHYDROFURANES
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α-Selenoalkyllithiums already used for the regioselective synthesis of epoxides are found valuable building blocks for the synthesis of higher homologues namely oxetanes and tetrahydrofuranes.The general synthetic strategy used is schematized below and re
- Sevrin, M.,Krief, A.
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p. 585 - 586
(2007/10/02)
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- A DIRECT PHENYLSELENENYLATION OF ALKYL HALIDES, ALKENYL SULFONATES, AND EPOXIDES BY AN ELECTROREDUCTION OF DIPHENYL DISELENIDE
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A convenient procedure for phenylselenenylation of alkyl halides, alkenyl sulfonates, and epoxides with phenyl selenide anion was accomplished by electroreduction of diphenyl diselenide in a protic solvent.
- Torii, Sigeru,Inokuchi, Tsutomu,Asanuma, Goro,Sayo, Noboru,Tanaka, Hideo
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p. 867 - 868
(2007/10/02)
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- A halide ion promoted electrochemical oxyselenenylation of olefins
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A novel electrolytic transformation of olefins 1 into oxyselenides 2 has been performed in high yields and high regioselectivities by elctrolyzing olefins in protic solvents (MeOH, AcOH, H2O-MeCN) containing Et4NX (X = Cl, Br, I) and diphenyl diselenide using platinum foils.
- Torii, Sigeru,Uneyama, Kenji,Ono, Michio
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p. 2741 - 2744
(2007/10/02)
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