1207173-53-2Relevant academic research and scientific papers
Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2
Huang, Wen-Bin,Ren, Fang-Yu,Wang, Ming-Wei,Qiu, Li-Qi,Chen, Kai-Hong,He, Liang-Nian
, p. 14109 - 14120 (2020)
Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the CC bond of propargylic amines with CO2 and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. This reaction proceeds under mild reaction conditions, which is operationally simple and scalable with a broad scope, exclusive selectivity, and good functional group compatibility. Mechanistic studies suggest a one-pot tandem cyclization/radical addition sequence, along with the phosphorylation/cyclization scheme.
Synthesis and Rearrangement of P-Nitroxyl-Substituted PIIIand PVPhosphanes: A Combined Experimental and Theoretical Case Study
Heurich, Tobias,Qu, Zheng-Wang,No?inovi?, Senada,Schnakenburg, Gregor,Matsuoka, Hideto,Grimme, Stefan,Schiemann, Olav,Streubel, Rainer
, p. 10102 - 10110 (2016/07/19)
Low-temperature generation of P-nitroxyl phosphane 2 (Ph2POTEMP), which was obtained by the reaction of Ph2PH (1) with two equivalents of TEMPO, is presented. Upon warming, phosphane 2 decomposed to give P-nitroxyl phosphane P-oxide 3 (Ph2P(O)OTEMP) as one of the final products. This facile synthetic protocol also enabled access to P-sulfide and P-borane derivatives 7 and 13, respectively, by using Ph2P(S)H (6) or Ph2P(BH3)H (11) and TEMPO. Phosphane sulfide 7 revealed a rearrangement to phosphane oxide 8 (Ph2P(O)STEMP) in CDCl3at ambient temperature, whereas in THF, thermal decomposition of sulfide 7 yielded salt 10 ([TEMP-H2][Ph2P(S)O]). As well as EPR and detailed NMR kinetic studies, indepth theoretical studies provided an insight into the reaction pathways and spin-density distributions of the reactive intermediates.
Enantioselective desymmetrization of diphenylphosphinamides via (-)-sparteine-mediated ortho-lithiation. synthesis of P-chiral ligands
Popovici, Cristinel,Ona-Burgos, Pascual,Fernandez, Ignacio,Roces, Laura,Garcia-Granda, Santiago,Iglesias, Maria Jose,Ortiz, Fernando Lopez
supporting information; experimental part, p. 428 - 431 (2010/04/24)
[Chemical equation presented] Asymmetric ortho-lithiation of N-dialkyl-P,P-diphenylphosphinamides using [n-BuLi·(-)-sparteine] is described as an efficient method for the synthesis of P-chiral ortho-functionalized derivatives in high yields and ee's from
