953-33-3Relevant academic research and scientific papers
Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations
Kovács, Szabolcs,Bayarmagnai, Bilguun,Aillerie, Alexandre,Goo?en, Lukas J.
, p. 1913 - 1918 (2018)
New late-stage phosphorothiolation methods are disclosed that allow the efficient transfer of SP(O)(OR)2 groups to diversely functionalized substrates using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammonium O,O-dimethyl phosphorothioate, was synthesized in near-quantitative yield from Me3SiP(O)(OMe)2, elemental sulfur and Me4NF. Its umpolung with N-bromophthalimide provided the electrophilic reagent, O,O-dimethyl-S-(N-phthalimido)phosphorothioate. Complementary methods based on these reagents enable the phosphorothiolation of diversely functionalized alkyl halides, arenediazonium salts, arylboronic acids and electron-rich arenes in good yields under mild conditions. (Figure presented.).
Reactions of Aromatic Diazonium Salts with Esters of Acrylic and Methacrylic Acids in the Presence of O,O′-Diethyl Phosphodithioates
Grishchuk,Gorbovoi,Kudrik,Ganushchak,Kaspruk
, p. 362 - 364 (2007/10/03)
Alkyl 2-(diethoxythiophosphorylthio)-2-phenylpropionates were prepared by reaction of aromatic diazonium salts with esters of acrylic and methacrylic acids in the presence of potassium O,O′-diethyl dithiophosphate in a water-acetone (1 : 2) medium. The reaction is accompanied by formation of aryl O,O′-diethyl phosphodithioates. The diethoxythiophosphorylthioarylation of acrylates readily occurs in the absence of copper salts, thus providing an example of a noncatalytic reaction of diazonium salts with unsaturated compounds in the presence of foreign nucleophiles.
