Reduced Species (HSO−2, SO·−2) Promoted One‐Pot Efficient Synthesis of Phenyl Alkyl Selenides

Tang, Ri‐Yuan; Zhong, Ping; Lin, Qiu-Lian

doi:10.1002/cjoc.200790104

Cited by 4 publications

(1 citation statement)

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“…A mechanism has been proposed previously for the reduction of disulfide 4a followed by the hydrothiolation of 1,4-diphenylbuta-1,3-diyne (3a) (Scheme 3). 6b, 14,16 Initially, rongalite (2) undergoes decomposition to form formaldehyde and HSO 2 in the presence of base followed by a single electron transfer to the disulfide to furnish the intermediates such as anionic species E and radical F. 14,16 The thiolate radical F further gets reduced to anionic species E, by another single electron transfer (SET) from the radical (HSO 2…”

Section: Paper Syn Thesismentioning

confidence: 99%

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Venkateswarlu

Chandrasekaran

2014

Synthesis

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India+ 9 1 ( 8 0 ) 2 3 6 0 0 5 2 9 scn@orgchem.iisc.ernet.in R 1 R 2 R 2 R 1 X H Ar A (Z-isomer) R 1 , R 2 = aryl, alkyl R 1 X H Ar R 2 Ar X H X = S, Se A HO S ONa O conditions: K 2 CO 3 , DMF-H 2 O (20:1) + Ar-X-X-Ar (0.5 equiv) 70 °C 40/50 °CAr-X-X-Ar (0.5 equiv)Ar-X-X-Ar (1 equiv) °CAbstract This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH 2 SO 2 Na) and potassium carbonate, buta-1,3-diynes undergo stereoselective addition of the thiolate or selenide anion generated in situ from diaryl disulfides or diselenides to afford the corresponding (Z)-1-sulfanyl-or (Z)-1-selanylalk-1-en-3-yne derivatives, respectively. The reaction of buta-1,3-diynes with diaryl disulfides or diselenides at higher temperature (70 °C) gave a mixture of monothiolation/selenation and bisthiolation/selenation products in moderate to good yields.

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Section: Paper Syn Thesismentioning

confidence: 99%

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Venkateswarlu

Chandrasekaran

2014

Synthesis

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Metal‐Free Photochemical C−Se Cross‐Coupling of Aryl Halides with Diselenides

Wang

Mao

et al. 2022

Adv Synth Catal

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A light-mediated CÀ Se bond coupling reaction of aryl halides with diselenides under mild photocatalyst-free conditions for preparing aryl selenoethers has been achieved. The transformation is charactered by readily available materials, mild conditions, broad substrate scope and high efficiency. A reasonable mechanism has been proposed based on the preliminary mechanistic investigation. The protocol is also suitable for forging CÀ S bond and CÀ Te bond by the use of disulfides and ditellurides.

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Reduced Species (HSO₂^‐, SO₂^×^‐) Promoted One‐Pot Efficient Synthesis of Phenyl Alkyl Selenides.

2007

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Reduced Species (HSO⁻₂, SO^·−₂) Promoted One‐Pot Efficient Synthesis of Phenyl Alkyl Selenides

Cited by 4 publications

References 41 publications

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Metal‐Free Photochemical C−Se Cross‐Coupling of Aryl Halides with Diselenides

Reduced Species (HSO₂^‐, SO₂^×^‐) Promoted One‐Pot Efficient Synthesis of Phenyl Alkyl Selenides.

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Reduced Species (HSO−2, SO·−2) Promoted One‐Pot Efficient Synthesis of Phenyl Alkyl Selenides

Cited by 4 publications

References 41 publications

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Metal‐Free Photochemical C−Se Cross‐Coupling of Aryl Halides with Diselenides