135440-57-2Relevant academic research and scientific papers
Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds
Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
, p. 7386 - 7392 (2020)
We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.
Ph2PI as a reduction/phosphination reagent: Providing easy access to phosphine oxides
Wang, Feijun,Qu, Mingliang,Chen, Feng,Xu, Qin,Shi, Min
, p. 8580 - 8582 (2012/09/22)
The reaction of aldehydes with Ph2PI provides a facile way to the synthesis of pentavalent phosphine compounds with moderate to good yields.
Studies on the efficient generation of phosphorus-carbon bonds via a rearrangement of PIII esters catalysed by trimethylhalosilanes
Dabkowski, Wojciech,Ozarek, Alfred,Olejniczak, Sebastian,Cypryk, Marek,Chojnowski, Julian,Michalski, Jan
experimental part, p. 1747 - 1756 (2009/09/25)
Halotrimethylsilanes Me3SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R′R″P-OR into the corresponding phosphoryl systems R′R″P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by 31P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno PIII structures R′R″PX and silyl ethers ROSiMe3 and that they subsequently react to give the corresponding phosphorus silyl esters - Me 3SiOPR′R″-and alkyl halides RX. At higher temperatures these intermediates then react to form R′R″P(P)R compounds. This paper also features the surprising observation that when esters Ph 2POR and halotrimethylsilanes Me3SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph2R2P+X - and trimethylsilyl diphenylphosphinate - Ph2P(O) OSiMe3 - are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me3SiCl is not reactive and this paper explains why.
The Synthesis of (Z)-Penta-2,4-dien-1-ol and Substituted (E)-Pentadienols by the Stereochemically Controlled Horner-Wittig Reaction
Brown, Paul S.,Greeves, Nicholas,McElroy, Andrew B.,Warren, Stuart
, p. 1485 - 1492 (2007/10/02)
Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol.Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction.The geometry of only one double bond can be controlled.
