1733-58-0Relevant academic research and scientific papers
X-ray crystallographic, luminescence and NMR studies of phenacyldiphenylphosphine oxide with the Ln(iii) ions Sm, Eu, Gd, Tb and Dy
Leach, Erin G.,Shady, Justin R.,Boyden, Adam C.,Emig, Anne-Lise,Henry, Alyssa T.,Connor, Emily K.,Staples, Richard J.,Schaertel, Stephanie,Werner, Eric J.,Biros, Shannon M.
, p. 15458 - 15469 (2017)
We report here the characterization in solution (NMR, luminescence, MS) and the solid-state (X-ray crystallography, IR) of complexes between phenacyldiphenylphosphine oxide and five Ln(iii) ions (Sm, Eu, Gd, Tb, Dy). Four single crystal X-ray structures are described here showing a 1:2 ratio between the Ln3+ ions Eu, Dy, Sm and Gd and the ligand, where the phosphine oxide ligands are bound in a monodentate manner to the metal center. A fifth structure is reported for the 1:2 Eu(NO3)3-ligand complex showing bidentate binding between the two ligands and the metal center. The solution coordination chemistry of these metal complexes was probed by 1H, 13C and 31P NMR, mass spectrometry, and luminescence experiments. The title ligand has the capability to sensitize Tb3+, Dy3+, Eu3+ and Sm3+ leading to metal-centered emission in solutions of acetonitrile and methanol and in the solid state.
Base-Promoted Direct Oxyphosphorylation of Alkynes with H-Phosphine Oxides in the Presence of Water
Zhong, Wenwu,Tan, Tao,Shi, Lei,Zeng, Xue
, p. 1379 - 1384 (2018)
We have developed a simple method for the oxyphosphorylation of arylalkynes to give β-keto phosphine oxides without the assistance of any transition metal. An inorganic base promoted the oxyphosphorylation and water played a synergistic role in the formation of various β-keto phosphine oxides. The reaction showed a wide structural scope and broad functional-group tolerance, and it proceeded under mild reaction conditions. This method solved the problem of metal dependence in the oxyphosphorylation of alkynes, providing a potential application in organic chemistry. Control experiments revealed the mechanism of the oxyphosphorylation and the synergistic role played by water in the radical process.
Silver-Catalyzed Aerobic Oxidative Decarboxylative Coupling of Arylpropiolic Acids with H-Phosphine Oxides: Mild and Facile Synthesis of β-Oxophosphine Oxides
Zeng, Yao-Fu,Tan, Dong-Hang,Lv, Wen-Xin,Li, Qingjiang,Wang, Honggen
, p. 4335 - 4338 (2015)
A silver-catalyzed oxidative decarboxylative coupling reaction of arylpropiolic acids with H-phosphine oxides by using air as the terminal oxidant was developed. The reaction proceeds smoothly under mild conditions to give β-oxophosphine oxides in moderate to good yields. Preliminary mechanistic studies were conducted. Aerobic oxidative decarboxylative coupling of arylpropiolic acids with H-phosphine oxides is realized under silver catalysis. The reaction proceeds smoothly under mild conditions to give β-oxophosphine oxides in moderate to good yields. Preliminary mechanistic studies are conducted.
A convenient approach to λ5-phosphinines via interaction of phosphorylated 3-pyrrolidinocrotonitrile with 2-bromoacetophenones
Svyaschenko, Yurii V.,Kostyuk, Alexandr N.,Barnych, Bogdan B.,Volochnyuk, Dmitriy M.
, p. 5656 - 5664 (2007)
The alkylation of 2-(diphenylphosphino)-3-pyrrolidin-1-ylbut-2-enenitrile with a set of bromoacetophenones has been studied. Cyclization of the phosphonium salts into 6-cyano-3-hydroxy-3-aryl-1,1-diphenyl-5-pyrrolidin-1-yl-1,2,3,4-tetrahydrophosphininium
Synthesis of tertiary phosphine oxides by alkaline hydrolysis of quaternary phosphonium zwitterions using excess t-BuOK and stoichiometric water
Zhong, Chun-Hong,Huang, Wenhua
supporting information, p. 1537 - 1546 (2021/01/07)
Hydrolysis of quaternary arylphosphonium zwitterions bearing COO? and those in situ generated from the corresponding salts bearing Ac or OH at the aryl ring by using excess t-BuOK and stoichiometric water affords tertiary arylphosphine oxides in moderate to excellent yield, in contrast to hydrolysis of these zwittertion or salts in aqueous NaOH that mainly provides phosphine oxides with the loss of the aryl group. Under the t-BuOK/water conditions, hydrolysis of carbonyl stabilized ylides Ph3P = CHCOR (R = Ph, Me, and OEt), which partially exist as phosphonium enolates, prefers to produce Ph2P(O)CH2COR. Further reduction of Ph2P(O)CH2COMe by PhSiH3 allows the preparation of Ph2PCH2COMe in 43% yield.
Silver-Catalyzed Oxyphosphorylation of Unactivated Alkynes
Liu, Binbin,Song, Qingmin,Liu, Zhaohong,Wang, Zikun
supporting information, p. 3214 - 3219 (2021/05/27)
Here, we describe an application of hydroazidation in the instant activation of alkynes for achieving the oxyphosphorylation of unactivated alkynes with diarylphosphinoyl radicals under mild reaction conditions. This reaction provides a method for accessing β-ketophosphine oxides and phosphorus-containing pyrroles. (Figure presented.).
Visible light-mediated photocatalytic phosphorylation of vinyl azides: A mild synthesis of β-ketophosphine oxides
Jung, Hye Im,Kim, Dae Young
, p. 380 - 387 (2019/12/24)
The photoredox-catalyzed phosphorylation of vinyl azides is described in this paper. The reaction proceeded smoothly using an inexpensive and easily-accessible Eosin Y as a photocatalyst under mild reaction conditions without any other oxidant, metal, or
Iron-Catalyzed and Air-Mediated C(sp3)?H Phosphorylation of 1,3-Dicarbonyl Compounds Involving C?C Bond Cleavage
Ou, Yingcong,Huang, Yuanting,Liu, Yu,Huo, Yanping,Gao, Yang,Li, Xianwei,Chen, Qian
supporting information, p. 5783 - 5787 (2020/11/30)
A C(sp3)?H phosphorylation has been achieved via the iron-catalyzed cross-coupling reactions between 1,3-dicarbonyl compounds and P(O)?H compounds involving C?C bond cleavages with air as the oxidant. This transformation provides a straightforward way to construct C(sp3)?P bonds, leading to the formation of β-ketophosphine oxides in up to 93% yield with good functional group tolerance. (Figure presented.).
Cobalt(II)-Catalyzed Bisfunctionalization of Alkenes with Diarylphosphine Oxide and Peroxide
Shen, Jian,Xiao, Bo,Hou, Yang,Wang, Xue,Li, Gui-Zhi,Chen, Jin-Chun,Wang, Wei-Li,Cheng, Jian-Bo,Yang, Bin,Yang, Shang-Dong
supporting information, p. 5198 - 5209 (2019/11/13)
The low-cost cobalt(II) catalyst has been used for the first time to achieve P(O)-radical-mediated bisfunctionalization of alkenes with diarylphosphine oxide and peroxides. This simple process is performed under mild conditions to afford a wide variety of phosphonation-peroxidation products in a one-pot manner. Computational studies are carried out to provide a theoretical support for the P(O)-radical-involved bisfunctionalization of alkenes. (Figure presented.).
An efficient preparation of β-ketophosphine oxides from alkynylphosphine oxides with benzaldehyde oxime as a hydroxide source
Chen, Lu-Lu,Zhang, Jing-Wen,Yang, Wan-Wan,Chen, Pei,Chen, Dan-Yun,Wang, Yan-Bo
, p. 3003 - 3009 (2019/03/20)
An effective and facile transitio-metal-free method has been developed for the synthesis of β-ketophosphine oxides from alkynylphosphine oxides with benzaldehyde oxime as a hydroxide surrogate. The current methodology provides simple access to various β-ketophosphine oxides in moderate to excellent yields with a broad substrate scope.
