Selenium

Krief, Alain

doi:10.1016/b978-008046519-7.00104-0

Cited by 39 publications

(14 citation statements)

References 459 publications

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“…We have explored in details the cross-coupling reaction of diaryl ditellurides with potassium aryltrifluoroborate salts using a catalytic amount of Cu(OAc) 2 /bpy in a mixture …”

Section: Discussionmentioning

confidence: 99%

“…Chalcogenide compounds have become attractive synthetic targets because of their chemo-, regio-, and stereoselective reactions, [1][2][3][4] used in a wide variety of functional groups, thus avoiding protection group chemistry and resulting in useful biological activities. [5][6][7] Therefore, many classes of organotellurium compounds have been prepared and studied to date and aryl-or vinylic tellurides are certainly the most useful and promising compounds in view of their usefulness in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts

Alves

Pena

Vieira

et al. 2009

J. Braz. Chem. Soc.

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Apresentamos aqui resultados das reações de acoplamento de diteluretos de diarila com sais de ariltrifluoroborato de potássio, usando quantidades catalíticas de Cu(OAc) 2 e bipiridina, em uma mistura de DMSO/H 2 O, sob ar atmosférico. Estas reações de acoplamento são gerais e são realizadas com diteluretos de diarila e sais de ariltrifluoroborato de potássio contendo substituintes neutros, retiradores e doadores de elétrons, fornecendo os correspondentes teluretos de diarila não simétricos em rendimentos de bons a excelentes.We present here results of the cross-coupling reaction of diaryl ditellurides with potassium aryltrifluoroborate salts using a catalytic amount of Cu(OAc) 2 and bypiridine in DMSO/H 2 O under air atmosphere. This cross-coupling reaction is general and was performed with diaryl ditellurides and potassium aryltrifluoroborate salts bearing electron-withdrawing, electron-donating and neutral substituents, affording the corresponding unsymmetrical diaryl tellurides in good to excellent yields.

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“…We have explored in details the cross-coupling reaction of diaryl ditellurides with potassium aryltrifluoroborate salts using a catalytic amount of Cu(OAc) 2 /bpy in a mixture …”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts

Alves

Pena

Vieira

et al. 2009

J. Braz. Chem. Soc.

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“…It can be considered the chemical chameleoneven more than the corresponding sulfur analog. In contrast to the similar sulfur derivatives with their identical variety of oxidation states, the weaker C-Sebond (234 kJ mol-I) [6], and the higher polarizability, nucleophilicity and oxidizability of selenium make the benzeneselenenyl group more useful. It may be introduced by nucleophilic, electrophilic, andless oftenby radical processes.…”

Section: Referencesmentioning

confidence: 99%

“…The haloselenenylation of alkenes 17 with benzeneselenenyl bromide (9) [5 I] or benzeneselenenyl chloride (6) [17, [52][53][54] in aprotic solvents provides the haloselenenylation products 18a (scheme 2). The addition proceeds exclusively in trans-manner due to the intervention of a selenium bridged cation (seleniranium ion) as a reaction intermediate.…”

Section: Addition To Double Bonds Selenocyclizationsmentioning

confidence: 99%

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Benzeneselenenyl Reagents in Organic Synthesis

Wessjohann

Sinks

1998

J. Prakt. Chem.

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An account of the most commonly used reagents for the introduction of the benzeneselenyl (phenyl seleno) group is given. The review focuses on the various methods of its introduction as auxiliary, modifying or protective entity, and its subsequent removal, thereby often promoting other reactions as cyclizations or double bond formation. Less emphasis is laid on reactions of the phenylselenenylated intermediates with the PhSe‐group left intact utilizing its stabilizing properties on charged intermediates, on reagents with a modified phenyl group, e.g. chiral derivatives, or on reactions not involving intermediate CSe‐bond formation.

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Mass spectral study of substituted allyl aryl and allyl alkyl selenides and some analogous sulfides

Prabhakar

Krishna

Kundu

et al. 1999

Rapid Commun. Mass Spectrom.

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The electron impact (EI) mass spectra of allyl aryl selenides showed abundant molecular ions and many fragment ions containing the selenium atom. alpha-Cleavage is the dominant process in the fragmentation of selenides, and cleavage product ions are characteristic of the substituents. In the case of 3-methyl allyl and related aryl selenides, characteristic delta-hydrogen migration to the selenium atom is observed. A McLafferty-type rearrangement is found in benzyl allyl selenides and substituted alkyl allyl selenides. The charge on the rearrangement products preferably remains on the fragments containing the phenyl group. The [M - SeH](+), [M - CH(3)](+) and [M - C(2)H(4)](+) ions are found only in the EI mass spectrum of allyl phenyl selenide, and are attributed to a Claisen rearrangement in the source of the mass spectrometer. All structurally informative fragmentation processes are supported by collision induced dissociation spectra of molecular ions. The fragmentation patterns found in methane chemical ionization (CI) spectra of the selenides were significantly different from those observed in EI. The EI and CI mass spectra of analogous sulfides showed similar behaviour to that observed in the corresponding selenides. Copyright 1999 John Wiley& Sons, Ltd.

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Selenium

Cited by 39 publications

References 459 publications

Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts

Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts

Benzeneselenenyl Reagents in Organic Synthesis

Mass spectral study of substituted allyl aryl and allyl alkyl selenides and some analogous sulfides

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