38868-16-5Relevant academic research and scientific papers
Copper-Catalyzed C?P Cross-Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange
Stankevi?, Marek,Wo?nicki, Pawe?
, p. 3484 - 3491 (2021/07/22)
An efficient protocol for concurrent tandem halogen exchange/C?P cross-coupling of cycloalkenyl bromides and secondary phosphine oxides has been developed. The catalytic system is based on cheap and air-stable copper(I) iodide as the precatalyst, commercially available N,N’-dimethylethylenediamine as the ligand, and Cs2CO3 or K2CO3 as the base. The use of sodium iodide as an additive reduces the excessive use of organic bromides to near-stoichiometric by promoting the in situ transformation to the corresponding iodides. Diarylphosphine oxides undergo cycloalkenylation with 35–99 % yields and dicyclohexylphosphine oxide with 30–53 % yields. In the case of acyclic alkenyl bromides the cross-coupling products undergo conjugate addition of diphenylphosphine oxide and satisfying yields are observed only for internal olefins. In the case of aryl bromides satisfying yields (43–72 %) are observed only for sterically unhindered arenes or arenes possessing an ortho-directing group. Cycloalkenylphosphine oxides prepared in the cross-coupling reaction undergo base-catalyzed and base-promoted conjugate addition to give bis(phosphinoyl)cycloalkanes.
Electrophilic and Nucleophilic Addition Reactions of α,β-Unsaturated Diphenylphosphoryl Compounds
Bichakhchyan, A. S.,Derdzyan, L. V.,Gasparyan, G. Ts.,Ovakimyan, M. Zh.,Poghosyan, A. S.
, p. 90 - 94 (2020/03/25)
Procedures were developed for the synthesis of diphenyl(prop-1-en-1-yl)phosphine oxide and cyclohex-1-en-1-yl(diphenyl)phosphine oxide by alkaline hydrolysis of triphenyl(prop-1-en-1-yl)phosphonium bromide and cyclohex-1-en-1-yl(triphenyl)phosphonim bromi
Synthesis of trivalent phosphorus derivatives by light-induced dibromophosphination of akenes
Krivchun,Khramchikhin
, p. 1527 - 1530 (2017/09/01)
Light-induced dibromophosphination of alkenes was studied. Dehydrobromination of the synthesized bromoalkylphosphonous dibromides gave the corresponding dibromophosphinoalkenes which were converted into alkenylphosphonous acids and their cyclic esters, benzo[1,3,2]dioxaphospholes.
β Effect of phophorus functionalities
Lambert, Joseph B.,Zhao, Yan
, p. 3156 - 3167 (2007/10/03)
Diphenylphosphinoyl (-P(=O)Ph2) and diphenylthiophosphinoyl (-P(=S)Ph2) respectively are modest and strong β-effect functionalities. When these groups are antiperiplanar to mesylate, the substrates solvolyze through unimolecular ioni
Reaction of Olefins with Dimethyl(methylthio)sulfonium Salts in the Presence of Triphenylphosphine. Preparation of Vinylphosphonium Salts
Okuma, Kentaro,Koike, Tetsufumi,Yamamoto, Shin-ichi,Takeuchi, Hiroshi,Yonekura, Kazuki,et at.
, p. 2375 - 2380 (2007/10/02)
Olefins were effectively converted into the corresponding (2-methylthioalkyl)triphenylphosphonium salts by the reaction with dimethyl(methylthio)sulfonium salts in the presence of triphenylphosphine. 2-Triphenylphosphonioalkyldimethylsulfonium salts, synt
REACTION OF TRIPHENYLPHOSPHINE RADICAL CATION WITH CYCLOALKENES: ELECTROCHEMICAL ONE-STEP PREPARATION OF 1-CYCLOALKENYLTRIPHENYLPHOSPHONIUM SALTS
Ohmori, Hidenobu,Takanami, Toshikatsu,Masui, Masaichiro
, p. 2199 - 2200 (2007/10/02)
Constant current electrolysis of triphenylphosphine in dichloromethane at a graphite anode in the presence of cycloalkenes gave the corresponding 1-cycloalkenylphosphonium salts in reasonable yields.
ENEPHOSPHINILATION
Mislankar, Dattatraya G.,Mugrage, Ben,Darling, S. D.
, p. 4619 - 4622 (2007/10/02)
A general method is described for the formation of vinylphosphines from arylsulfonylhydrazones.Oxidation of the resulting vinylphosphines yields phosphine oxides.
