159386-46-6Relevant academic research and scientific papers
Resorcin[4]arene-derived mono- And diphosphines in suzuki cross-coupling
Moll, Hani El,Semeril, David,Matt, Dominique,Toupet, Loic
, p. 901 - 908 (2010)
Three resorcin[4]arene cavitands (1-3) having either one or two resorcinolic C-2 atoms substituted by a -CH2PPh2 podand arm were assessed in the Suzuki arylation of aryl bromides with phenylboronic acid. Using P:Pd ratios of 2:1 and operating in dioxane at 100°C with a catalyst loading of 0.001 mol% resulted in highly efficient catalytic systems. For example, TOFs up to 34570 mol(converted ArBr)-mol(Pd)-1.h -1 were obtained with the proximally-disubstituted cavitand 3 when using 4-bromotoluene as substrate. The performance was shown to vary in the following order: monophosphine 1diphosphine 2 diphosphine 3 (where 2 is the distally disubstituted cavitand). A comparison of the catalytic properties of monophosphine-cavitand 1 with those of benzyldiphenylphosphine and o-anisylmethyldiphenyl phosphine suggests that 1 functions as a hemilabile phosphine, the oxygen atoms close to the phosphorus atom behaving as donors able to temporarily increase the electron density on the metal and/ or favour the formation of mono-ligand Pd(O) species.
Copper-catalyzed C–P cross-coupling of arylmethyl quaternary ammonium salts via C–N bond cleavage
Li, Nutao,Chen, Feng,Wang, Guanghui,Zeng, Qingle
, p. 99 - 106 (2020)
Abstract: A ligand-free copper-catalyzed C–P cross-coupling reaction of arylmethyl quaternary ammonium salts and diarylphosphine oxides in air is developed. Arylmethyl quaternary ammonium salts with various functional groups and a variety of dialkyl- and diarylphosphine oxides afford C–P cross-coupling products with good yields. This protocol requires no inert atmosphere, no ligand, and simple operation steps. Graphic abstract: [Figure not available: see fulltext.].
Preparation method of aryl methyl phosphine acylate
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Paragraph 0040, (2019/10/01)
The invention discloses a preparation method of aryl methyl phosphine acylate. The method uses (hetero) aryl acetic acid as the starting material, and the raw materials are easily available and have agreat variety. The product obtained by the method provided by the invention has various types and wide uses. The aryl methyl phosphine acylate can be easily converted into a bis (hetero)arylethene derivative, and the compound can be used for preparation of dyes, fluorescent agents, whiteners, light-emitting diodes and other devices. In addition, the method disclosed by the invention has the advantages of easily available, stable and low toxicity raw materials, mild reaction conditions, high yield of target product, low pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.
Trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement
Renard, Pierre-Yves,Vayron, Philippe,Mioskowski, Charles
, p. 1661 - 1664 (2007/10/03)
(Matrix presented) We describe a new, straightforward, and easy-to-handle method for achieving an unprecedented trimethylsilyl halide-catalyzed Michaelis-Arbuzov-like rearrangement. This rearrangement occurs at temperatures from room temperature to 80°C and does not require addition of any alkyl halide. The scope and limitations of this new reaction are explored, as well as its mechanism.
Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement
Renard, Pierre-Yves,Vayron, Philippe,Leclerc, Eric,Valleix, Alain,Mioskowski, Charles
, p. 2389 - 2392 (2007/10/03)
The taming of the shrew! For the first time, a broadly applicable efficient room-temperature Arbuzov rearrangement is described. This reaction is accomplished through an atom-economical Lewis acid catalyzed process (see scheme, TMSOTf=trimethylsilyl trifluoromethane-sulfonate). The method has been generalized to primary and activated secondary phosphites, phosphinites, and phosphonites.
Photochemistry of Substituted Benzyldiphenylphosphine Oxides
Zhao, Ningning,Neckers, Douglas C.
, p. 2145 - 2150 (2007/10/03)
Photochemical reactions (λ irr = 54 nm) of substituted benzyldiphenylphosphine oxides 1a-e have been investigated in benzene and acetonitrile. α-Cleavage from the singlet excited state is proposed as the primary process, and products formed bot
PHOSPHORUS-CONTAINING PODANDS. XII. EFFECT OF ALKYL AND PHENYL SUBSTITUENTS ON THE PHOSPHORUS ATOM ON THE COMPLEXING POWER OF NEUTRAL MONOPODANDS. "ANOMALOUS ALKYL EFFECT"
Evreinov, V. I.,Baulin, V. E.,Vostroknutova, Z. N.,Safronova, Z. V.,Bondarenko, N. A.,Tsvetkov, E. N.
, p. 190 - 197 (2007/10/03)
The stability constants of M+L complexes with monopodands o-RC6H4O(CH2CH2O)nC6H4R-o were determined by conductometry in the mixed solvent THF-CHCl3 (4:1, v/v) at 25 deg C.The results obtained were compared with data for previously studied monopodands with a similar structure but with phenyl substituents at the phosphorus.An anomalous phenomenon, viz., influence of terminal alkyl groups on the efficiency of monopodands ("anomalous alkyl effect"), was observed, which consists of a noticeable, and sometimes dramatic, decrease in the stability constants upon replacement of electron-acceptor substituents at the phosphorus by electron-donor alkyl groups, which contradicts the expected dependence of the complexing power of unidentate phosphoryl compunds on their structure.Procedures for synthesizing monopodands, fragments of their terminal groups, and some initial compounds are described.
Efficient synthesis of benzylphosphine oxides and E-stilbenes
Brown,Brown, Karen M.,Lawrence,Lawrence, Nicholas J.,Liddle,Liddle, John,Muhammad,Muhammad, Faiz,Jackson,Jackson, David A.
, p. 6733 - 6736 (2007/10/02)
A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.
