6591-07-7Relevant articles and documents
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
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.
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