Effect of phosphine and phosphine sulfide ligands on the cobalt-catalyzed reductive coupling of 2-iodobutane with n-butyl acrylate

Aizawa, Shiro; Fukumoto, Koji; Kawamoto, Tatsuya

doi:10.1016/j.poly.2013.06.013

Cited by 12 publications

(1 citation statement)

References 34 publications

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“…Tertiary phosphine sulfides and selenides constitute an important class of organophosphorus compounds . They are widely used as popular precursors and stabilizing agents for semiconductive nanoparticles , extractants of noble metal ions , versatile ligands for metal complexes (including catalysts ) as well as reagents for organic synthesis . In addition, tertiary phosphine sulfides are offered as additives to electrolytes , modifiers for rubbers , and sensitizers in photographic materials .…”

Section: Introductionmentioning

confidence: 99%

Straightforward Solvent‐Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron‐Rich Alkenes, and Elemental Sulfur or Selenium

Artem’ev

Чернышeва

Yas’ko

et al. 2015

Heteroatom Chemistry

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A series of tertiary phosphine sulfides and selenides have been synthesized in excellent yields (88‐99%) via a three‐component reaction between secondary phosphines, electron‐rich alkenes (styrene, vinyl chalcogenides), and elemental sulfur or selenium, proceeding under solvent‐free conditions (80‐82°C, 4–44 h). The interaction occurs via initial oxidation of secondary phosphines with elemental sulfur or selenium followed by noncatalyzed anti‐Markovnikov addition of the generated R2P(E)H (E = S, Se) species to alkenes to afford the corresponding adducts with high chemo‐ and regioselectivity.

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Section: Introductionmentioning

confidence: 99%

Straightforward Solvent‐Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron‐Rich Alkenes, and Elemental Sulfur or Selenium

Artem’ev

Чернышeва

Yas’ko

et al. 2015

Heteroatom Chemistry

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Acetylacetonate and Acetate Complexes of Nickel(II) Catalyse the Air Oxidation of Phosphines

et al. 2020

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The polymeric complex trans‐[Ni(acac)2(µ2‐dppe)]n·2MeCN {1a, dppe = 1,2‐ethylenebis(diphenylphosphine)} is sometimes transiently deposited from the reaction of [Ni(acac)2] with dppe in MeCN prior to its facile onwards air oxidation to final crystallization of a doubly‐oxygenated relative, cis‐[Ni(acac)2(µ2‐dppeO2)]n {2, dppeO2 = 1,2‐ethylenebis(diphenylphosphineoxide)}. A similar unsolvated phase of the initial polymer, trans‐[Ni(acac)2(µ2‐dppe)]n (1b), can be isolated from toluene. The oxidation of dppe by O2 is catalytic and dppeO2 was isolated in close to stoichiometric yields from solutions containing 5 % Ni(acac)2 relative to dppe. The reaction rate slows after a few turnovers due to inhibition by the product. The relative yields of dppeO2 are higher than those from catalytic air oxidation of methyldiphenylphosphine and triphenylphosphine and we speculate that a pathway for this reaction involves a dimetallic cooperativity enabled specifically by dppe.

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Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

Малышева¹,

Гусарова²,

Artem’ev³

et al. 2014

Eur J Org Chem

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An atom‐economic green synthesis of tertiary phsophine sulfides has been developed based on catalyst‐ and solvent‐free addition of secondary phosphine sulfides to diverse terminal and internal alkenes (hept‐1‐ene, cyclohexene, styrenes, allyl alcohol, vinyl ethers, vinyl sulfides, vinyltrimethylsilane, 1‐vinylimidazoles, vinyl acetate). The reaction proceeds under mild conditions (80 °C, without solvent, 4–45 h) to afford chemo‐ and regioselectively the corresponding anti‐Markovnikov adducts in excellent to quantitative yields (50–99 %).

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Effect of phosphine and phosphine sulfide ligands on the cobalt-catalyzed reductive coupling of 2-iodobutane with n-butyl acrylate

Cited by 12 publications

References 34 publications

Straightforward Solvent‐Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron‐Rich Alkenes, and Elemental Sulfur or Selenium

Straightforward Solvent‐Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron‐Rich Alkenes, and Elemental Sulfur or Selenium

Acetylacetonate and Acetate Complexes of Nickel(II) Catalyse the Air Oxidation of Phosphines

Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

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