- α-Alkylation of tertiary amines by C(sp3)–C(sp3) cross-coupling under redox neutral photocatalysis
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Direct α-alkylation of N-phenyl-tetrahydroisoquinoline with alkyl selenides of desired alkyl chain length and functionality is reported by photoredox catalysis. Construction of hexahydro pyrrolo- and pyrido-isoquinoline scaffolds along with indolines and tetrahydroquinolines is also described by intramolecular C(sp3)–C(sp3) cross-couplings.
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana
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supporting information
p. 4480 - 4483
(2016/09/14)
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- Highly regioselective hydroselenation of inactivated terminal alkynes using diselenide-Ph2P(O)H mixed systems under visible-light irradiation
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Upon visible-light irradiation, we could achieve a highly regioselective hydroselenation of inactivated terminal alkynes to give 1-(organylseleno)-1- alkenes by using diselenide-Ph2P(O)H mixed systems. The photoinduced hydroselenation presented in this study is advantageous as it does not involve the handling of oxygen-sensitive and foul-smelling selenols.
- Kobiki, Yohsuke,Kawaguchi, Shin-Ichi,Ogawa, Akiya
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p. 5453 - 5456
(2013/09/23)
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- A simple zinc-mediated preparation of selenols
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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.
- Santi, Claudio,Santoro, Stefano,Testaferri, Lorenzo,Marcello Tiecco
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scheme or table
p. 1471 - 1474
(2009/04/07)
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- Odorless diphenyl diselenide and disulfide: Syntheses and applications
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Bis[4-(trimethylsilyl)phenyl]diselenide (3) and bis[4-(trimethylsilyl) phenyl]disulfide (31) are found to be odorless equivalents of the commonly used diphenyl diselenide and diphenyl disulfide, respectively. The diselenide 3 is shown to be useful in the preparation of odorless selenium(II) chloride 26 and selenium(IV) trichloride 28 that follow similar reactivity patterns to their phenyl derivatives and can be stored refrigerated under dry conditions. The corresponding selenium(II) bromide had to be prepared fresh from 3 before use. It is also shown that the trimethylsilyl group in the sulfide products can be protodesilylated quantitatively using TFA. Georg Thieme Verlag Stuttgart.
- Patra, Pranab K.,Shanmugasundaram, Kandasamy,Matoba, Manabu,Nishide, Kiyoharu,Kajimoto, Tetsuya,Node, Manabu
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p. 447 - 457
(2007/10/03)
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- Reaction of organic selenocyanates with hydroxides: The one-pot synthesis of dialkyl diselenides from alkyl bromides
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The amount of hydroxide used in the reaction with organic selenocyanate determines the identity of the product (see scheme). Dialkyl and diaryl diselenides are efficiently prepared with 0.5 equivalents of hydroxide, whereas the reaction of aryl selenocyanates with at least one molar equivalent of hydroxide leads to the formation of aryl selenolates, R = Ph, Bu, iPr, PhCH2; M = Li, Na, K.
- Krief, Alain,Dumont, Willy,Delmotte, Cathy
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p. 1669 - 1672
(2007/10/03)
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- Reductive Cleavage of the Se-Si Bond in Aryiselenotrimethylsilanes: Novel Method for the Synthesis of Unsymmetrical Selenides
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Arylseienotrimethylsilanes are reduced by samarium diiodide to yield samarium areneselenolates, which react with alkyl halidesto give unsymmetrical selenides.
- Zhang, Songlin,Zhang, Yongmin
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p. 350 - 351
(2007/10/03)
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- A convenient procedure for the preparation of organic selenides
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Treatment of diphenyl diselenide with tributylphosphine in an alkaline medium forms phenylselenolate ion which converts alkyl halides, α,β-unsaturated ketones, and epoxides into alkyl selenides, (phenylseleno)alkenones, and β-(phenylseleno)alkanols, respe
- Sakakibara,Katsumata,Watanabe,Toru,Ueno
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p. 377 - 379
(2007/10/02)
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- SYNTHESIS OF α-SELENOALKYLLITHIUM COMPOUNDS
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α-Phenylselenoalkyllithiums and α-methylselenoalkyllithiums have been prepared from the corresponding selenoacetals and alkyllithiums.Several features of this reaction are disclosed.For example, the reaction is more readily achieved on phenylselenoacetals than on methylseleno analogues.Those derived from hindered carbonyl compounds are less readily cleaved. s-BuLi/THF proved superior to n-BuLi in THF, itself better than n-BuLi in ether.
- Krief, A.,Dumont, W.,Clarembeau, M.,Bernard, G.,Badaoui, E.
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p. 2005 - 2022
(2007/10/02)
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- Novel Functional Group Transformations involving Alkyl Phenyl Selenones
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Alkyl phenyl selenones readily undergo substitution reactions, and are valuable precursors of epoxides on reaction with aldehydes inthe presence of bases.
- Krief, Alain,Dumont, Willy,Denis, Jean-Noel
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p. 571 - 572
(2007/10/02)
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- Phenyl Selenide Anion, a Superior Reagent for the SN2 Cleavage of Esters and Lactones
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The scope and limitations of SN2-type cleavages of esters and lactones with phenyl selenide anion are discussed.The reagent, when generated properly, is found to be an extremely potent nucleophile.However, its nucleophilicity can be greatly attenuated by varying the counterion and/or the degree of solvation of the anion.The reagent can be used in the presence of a variety of functional groups and exhibits a high degree of selectivity; e.g., methyl esters are selectively cleaved in the presence of ethyl esters.As the hindrance around the carbinol carbon increases, products derived from acyl oxygen cleavage are observed.The mechanistic implications of this are discussed.
- Liotta, Dennis,Sunay, Ustun,Santiesteban, Hector,Markiewicz, William
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p. 2605 - 2610
(2007/10/02)
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- Phosphorus Tri-iodide (PI3), a Powerful Deoxygenating Agent
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On reaction with PI3 sulphoxides, selenoxides, aldehyde oximes, and primary nitroalkanes are transformed to sulphides, selenides, and nitriles, respectively.
- Denis, Jean Noel,Krief, Alain
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p. 544 - 545
(2007/10/02)
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