6591-07-7Relevant academic research and scientific papers
Phosphinoyl and thiophosphinoylcarbodithioates: Synthesis, molecular structure, and application as new efficient mediators for RAFT polymerization
Mazires, Stphane,Kulai, Ihor,Geagea, Roland,Ladeira, Sonia,Destarac, Mathias
, p. 1726 - 1734 (2015)
New phosphinoyl and thiophosphinoylcarbodithioates were synthesized in a one-pot reaction from the corresponding phosphinochalcogenides. Compounds of this new generation of thiocarbonylthio derivatives have been fully characterized by IR as well as 1
A structural and theoretical study of the thiophosphinite and dithiophosphinate anions
Mansfield, Natalie E.,Coles, Martyn P.,Hitchcock, Peter B.
, p. 2685 - 2702 (2008)
Two novel lithium compounds containing either the phosphorus-chalcogenide anions [Ph2PS]- or [Cy2PS2]- were isolated as decomposition products in the attempted formation of phospha(V)guanidinate anions. Lithium diphenylthiophosphinite was structurally cha
Metal-free SHNcross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes
Volkov, Pavel A.,Telezhkin, Anton A.,Khrapova, Kseniya O.,Ivanova, Nina I.,Albanov, Alexander I.,Gusarova, Nina K.,Trofimov, Boris A.
, p. 6206 - 6219 (2021/04/16)
Terminal acylacetylenes, typical electron-deficient acetylenes, drive SHNcross-coupling of pyridines with secondary phosphine chalcogenides under metal-free mild conditions (20-75 °C) to afford 4-chalcogenophosphorylpyridines in up to 70% yield. The reaction proceedsvia2,4-migration of chalcogenophosphoryl groups in the intermediate 1-acylvinyl-2-phosphoryl dihydropyridines with simultaneous redox elimination of the vinyl ketone oligomers. These results are generalized in a concept of trimodal (polarization/deprotonation/oxidation) catalyst-like assistance of electron-deficient acetylenes in SHNreaction of the pyridinoid heterocycles with PH-nucleophiles, which comprises: (i) repolarization (umpolung) of the pyridine ring, (ii) deprotonation of secondary phosphine chalcogenides to generate phosphorus-centered anions and (iii) oxidation of the dihydro intermediates.
Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants
Trofimov, Boris A.,Volkov, Pavel A.,Khrapova, Kseniya O.,Telezhkin, Anton A.,Ivanova, Nina I.,Albanov, Alexander I.,Gusarova, Nina K.,Chupakhin, Oleg N.
supporting information, p. 3371 - 3374 (2018/04/05)
Pyridines undergo site selective cross-coupling with secondary phosphine chalcogenides (oxides, sulfides, and selenides) in the presence of acylphenylacetylenes under metal-free mild conditions (70-75 °C, MeCN) to afford 4-chalcogenophosphoryl pyridines in up to 71% yield. In this new type of SNHAr reaction acylacetylenes act as oxidants, being stereoselectively reduced to the corresponding olefins of the E-configuration.
Synthesis of Phosphine Chalcogenides Under Solvent-Free Conditions Using a Rotary Ball Mill
Kumar, Rajnish,Kumar, Saurabh,Pandey, Madhusudan K.,Kashid, Vitthalrao S.,Radhakrishna, Latchupatula,Balakrishna, Maravanji S.
, p. 1028 - 1037 (2018/02/26)
The mechanochemical technique of ball milling has been applied to the solventless and eco-friendly synthesis of chalcogenides (sulfide and selenide) of a variety of tertiary and aminophosphines. In most of the cases, the products are obtained in almost quantitative yields with high purity by applying a simple workup procedure without using chromatographic techniques or any other purification methods. The scope of this methodology was explored by using a range of phosphines (mono, di and tetra) to synthesize partial as well as mixed chalcogenides. The use of almost equimolar amounts of starting materials and the absence of any byproducts significantly simplifies the product isolation compared with the standard solution state reactions, thus providing a highly atom economic (100 %) method with an ideal E-factor (E = 0). The solid-state reactions were monitored by 31P{1H} NMR spectroscopy. The structures of some of the products are also confirmed by single-crystal X-ray analyses. Although most of the reactions were carried out on ca. 100-mg scale, the scaling up of the reaction did not affect the course of the reaction.
Diastereoselective synthesis of N-sulfinyl α-aminophosphine sulfides and phosphines
Zhang, Wei,Gilbertson, Scott R.
supporting information, p. 2175 - 2177 (2017/05/16)
The diastereoselective synthesis of N-sulfinyl α-aminophosphine sulfides and phosphines is reported. These molecules are synthesized by formation of sulfinyl imine followed by diastereoselective addition of a diphenylphosphine sulfide. The product N-sulfinyl α-aminophosphine sulfides can be converted to phosphines through removal of the sulfur by reaction with Raney nickel. Hydrolysis of the sulfinyl group provides an amine that can then be attached to other ligands or structural scaffolds.
Non-catalyzed addition of secondary phosphine chalcogenides to divinyl chalcogenides under solvent-free conditions
Gusarova, Nina K.,Chernysheva, Nataliya A.,Yas’ko, Svetlana V.,Klyba, Lyudmila V.,Trofimov, Boris A.
, p. 488 - 500 (2016/10/03)
Secondary phosphine chalcogenides, R2PX (R═(CH2)2Ph, Ph; X = S, Se), react with divinyl chalcogenides, (CH2═CH)2Y (Y = S, Se, Te), at the 2:1 molar ratio (80–82°C, 56–80?h) in the absence of both cata
Green synthesis of tertiary alkylselanylphosphine chalcogenides via catalyst-and solvent-free addition of secondary phosphine chalcogenides to vinyl selenides
Gusarova,Chernysheva,Yas'Ko,Trofimov
, p. 526 - 534 (2015/10/19)
Secondary phosphine sulfides and phosphine selenides react with vinyl selenides under mild conditions (80-82°C, without catalyst and solvent) to form regioselectively functionalized anti-Markovnikov adducts in high yield.
An expedient access to γ-ketophosphine chalcogenides via the chemo-and regioselective addition of secondary phosphine chalcogenides to β,γ-ethylenic ketones
Artem’Ev, Alexander V.,Malysheva, Svetlana F.,Belogorlova, Nataliya A.,Protzuk, Nadezhda I.,Albanov, Alexander I.,Bagryanskaya, Irina Y.,Schmidt, Elena Y.,Gusarova, Nina K.,Trofimov, Boris A.
, p. 455 - 462 (2018/01/18)
γ-Ketophosphine chalcogenides, precursors for plethora of novel functionalized phosphine chalcogenides and phosphines, are synthesized by chemo-and regioselective addition of secondary phosphine chalcogenides to β,γ-ethylenic ketones under catalyst-and so
Facile non-catalyzed synthesis of tertiary phosphine sulfides by regioselective addition of secondary phosphine sulfides to alkenes
Malysheva, Svetlana F.,Gusarova, Nina K.,Artem'Ev, Alexander V.,Belogorlova, Nataliya A.,Albanov, Alexander I.,Borodina, Tatyana N.,Smirnov, Vladimir I.,Trofimov, Boris A.
supporting information, p. 2516 - 2521 (2014/05/06)
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, vin
