13440-07-8Relevant academic research and scientific papers
Visible-light-driven metal-free aerobic synthesis of highly diastereoselective phosphinoylpyrroloindoles
Gorre, Ramesh,Enagandhula, Damodar,Balasubramanian, Sridhar,Akondi, Srirama Murthy
supporting information, p. 1354 - 1358 (2020/03/03)
A visible-light-driven metal-free phosphorus radical mediated construction of 2-phosphinoyl-3H-pyrrolo[1,2,a]indoles is described. This mild tandem phosphinoylation/cyclization protocol utilizes air as a green oxidant and proceeds in a short span of time at room temperature with high functional group tolerance, and excellent chemo- A nd diastereoselectivity.
An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
Cheng, Feixiang,Liu, Jianjun,Liu, Teng,Yu, Rong,Zhang, Yanqiong
, p. 253 - 262 (2019/12/28)
An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.
Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions
Liu, Weiping,Sahoo, Basudev,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information, p. 11673 - 11677 (2018/09/10)
The first cobalt-catalyzed hydrogenative N-methylation and alkylation of amines with readily available carboxylic acid feedstocks as alkylating agents and H2 as ideal reductant is described. Combination of tailor-made triphos ligands with cobalt(II) tetrafluoroborate significantly improved the efficiency, thus promoting the reaction under milder conditions. This novel protocol allows for a broad substrate scope with good functional group tolerance, even in the presence of reducible alkenes, esters, and amides.
Metal-Free Electrophilic Phosphination/Cyclization of Alkynes
Unoh, Yuto,Hirano, Koji,Miura, Masahiro
supporting information, p. 6106 - 6109 (2017/05/09)
A metal-free electrophilic phosphination reaction has been developed. Electrophilic phosphorus species generated in situ from secondary phosphine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleophiles to afford the corresponding phosphinated cyclization products in good yield. Preliminary NMR studies show that phosphirenium species may be involved as intermediates of the cyclization reactions.
Reaction of 1-bromonaphthalene with PH3 in the t-BuOK/DMSO system: PCl3-free synthesis of di(1-naphthyl)phosphine and its oxide
Kuimov, Vladimir A.,Matveeva, Elena A.,Khutsishvili, Spartak S.,Vakul'skaya, Tamara I.,Sinegovskaya, Lidiya M.,Malysheva, Svetlana F.,Gusarova, Nina K.,Trofimov, Boris A.
, p. 4723 - 4729 (2017/07/17)
The phosphine, generated together with hydrogen from red phosphorus and aqueous KOH, reacts with 1-bromonaphthalene in the t-BuOK/DMSO system under mild conditions (70 °C, atmospheric pressure) to give di(1-naphthyl)phosphine, which is easily oxidized in the presence of air to afford di(1-naphthyl)phosphine oxide in 45% preparative yield. Tri(1-naphthyl)phosphine and naphthalene are also formed in the reaction in 23 and 27% yield, respectively. According to ESR and UV data, the studied phosphination of 1-bromonaphthalene involves a single electron transfer process.
Asymmetric Morita–Baylis–Hillman Reaction: Catalyst Development and Mechanistic Insights Based on Mass Spectrometric Back-Reaction Screening
Isenegger, Patrick G.,B?chle, Florian,Pfaltz, Andreas
supporting information, p. 17595 - 17599 (2016/11/28)
An efficient protocol for the evaluation of catalysts for the asymmetric Morita–Baylis–Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of methyl acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate- and enantioselectivity-determining.
Catalytic enantioselective synthesis of sterically demanding alcohols using di(2°-alkyl)zinc prepared by the refined Charette's method
Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki
supporting information; experimental part, p. 5443 - 5445 (2010/10/04)
A highly practical, catalytic enantioselective 2°-alkyl addition to aldehydes and ketones was developed. Chiral phosphoramide ligand (1) with salt-free and solvent-free di(2°-alkyl)zinc reagents prepared from (2°-alkyl)MgCl was essential. The Royal Society of Chemistry 2010.
PROCESS FOR PRODUCTION OF PHOSPHINE-BORANE COMPLEXES
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Page/Page column 7, (2008/06/13)
A process for the production of phosphine-borane complexes represented by the general formula: or salts thereof: [wherein R1, R2 and R3 are each independently a hydrogen atom, a halogen atom, an optionally substituted alky
Asymmetric Hydroformylation of Vinyl Acetate with DIOP-Type Ligands
Hobbs, Charles F.,Knowles, W. S.
, p. 4422 - 4427 (2007/10/02)
The rhodium-catalyzed hydroformylation of vinyl acetate and related esters was carried out in the presence of chiral phosphine ligands of the DIOP type to give the corresponding optically active 2-(acyloxy)propanal, a precursor for the amino acid threonine.Ligand structure and the ligand/metal ratio were the primary factors controlling asymmetric induction; temperature, CO pressure, and solvent polarity had minor effects.The highest induction efficiencies, up to 51 percent ee, were obtained with the 5H-dibenzophospholyl derivative of DIOP (DIPHOL, 1e).
