889-57-6Relevant academic research and scientific papers
Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Lambert, Tristan H.,Steiniger, Keri A.
, p. 8013 - 8017 (2021/10/25)
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
Photoinduced selective hydrophosphinylation of allylic compounds with diphenylphosphine oxide leading to γ-functionalized P-ligand precursors
Tran, Dat Phuc,Sato, Yuki,Yamamoto, Yuki,Kawaguchi, Shin-ichi,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
, p. 3067 - 3078 (2021/04/19)
A series of bifunctional phosphine compounds promising as γ-functionalized phosphine ligand precursors are conveniently synthesized by the radical addition of diphenylphosphine oxide (Ph2P(O)H) to allylic compounds under photoirradiation. The p
Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines
Warner, Christopher J.A.,Berry, Sian S.,Jones, Simon
, (2019/11/11)
A series of bifunctional phosphine oxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asymmetric hydrosilylation of ketimines. bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide displayed the highest enantioselectivity of 60%.
Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors
Binyamin, Iris,Meidan-Shani, Shoval,Ashkenazi, Nissan
supporting information, p. 1332 - 1339 (2015/08/24)
The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosp
A silver-initiated free-radical intermolecular hydrophosphinylation of unactivated alkenes
Li, Zejiang,Fan, Fenghua,Zhang, Zengyan,Xiao, Yingxia,Liu, Dong,Liu, Zhong-Quan
, p. 27853 - 27856 (2015/03/31)
A scalable, operationally easy intermolecular hydrophosphinylation of various unactivated alkenes with H-P(O) compounds via an Ag(i)-initiated free radical process was developed. Mechanistic studies including electron-spin-resonance (ESR) and radical clock experiments suggest that atom transfer processes were involved in this system.
Hydrophosphinylation of unactivated alkenes with secondary phosphine oxides under visible-light photocatalysis
Yoo, Woo-Jin,Kobayashi, Shu
supporting information, p. 1844 - 1848 (2013/09/24)
A visible light induced hydrophosphinylation of unactivated alkenes with diaryl phosphine oxides was found to occur with good yields and under mild reaction conditions in the presence of an inexpensive and commercially available organic dye as a photocatalyst.
Synthesis and biological activity of dialkylamino-substituted phosphine oxides
Yarkevich,Petrova,Bachurin
, p. 1659 - 1664 (2013/02/23)
A series of dialkylamino-substituted phosphine oxides was synthesized and their physiological activity was studied. Pleiades Publishing, Ltd., 2012.
Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes
Clarke, Celia,Foussat, Stephanie,Fox, David J.,Pedersen, Daniel Sejer,Warren, Stuart
supporting information; experimental part, p. 1323 - 1328 (2009/12/04)
The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from β-alkyl, γ-benzoyl phosphine oxides via a three-step cascade reaction incorporating an acyl transfer, phosphinoyl transfer and cyclisation to form the cyclopropane. Using Evans' chiral oxazolidinone auxiliary and by masking the phosphine oxide moiety as a phosphine borane we have extended the method to the synthesis of enantiomerically-enriched trans-disubstituted cyclopropyl ketones.
The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes
Clarke, Celia,Fox, David J.,Pedersen, Daniel Sejer,Warren, Stuart
supporting information; experimental part, p. 1329 - 1336 (2009/12/04)
Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.
ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles
Ju-Nam, Yon,Allen, David W,Gardiner, Philip H.E.,Bricklebank, Neil
body text, p. 3504 - 3508 (2009/02/05)
Two new ω-thioacetylalkylphosphonium salts that function as masked cationic alkanethiolate ligands for the stabilisation of gold nanoparticles have been prepared. Both (3-thioacetylpropyl)triphenylphosphonium bromide and (6-thioacetylhexyl)triphenylphosphonium bromide were shown to form water-soluble gold nanoparticles of ca. 5-10 nm in size that are stable for up to six months. The related (3-thioacetylpropyl)diphenylphosphine oxide was also prepared but did not act as a stabilising ligand in gold nanoparticle formation.
