60324-15-4Relevant 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.
Free-Radical Phosphorylation of Olefins Initiated by Anodic Oxidation
Romakhin,Kosachev,Zagumennov,Nikitin
, p. 227 - 234 (2007/10/03)
Electrochemical oxidation of lithium and sodium dialkyl phosphites generates dialkyl phosphonyl radicals, which initiate chain free-radical addition of dialkyl phosphites across the alkene multiple bond to form alkyl(cycloalkyl)phosphonates. Alkyl(cycloalkyl)phosphonates are formed simultaneously owing to anodic oxidation of adsorbed primary radical adducts of phosphonyl radical and alkene molecule to give the carbenium cation, followed by deprotonation of the latter.
A new and efficient synthesis of α-amino cycloalkylphosphonic acids via electrophilic azidation of cycloalkylphosphonates
Gueguen, Catherine,About-Jaudet, Elie,Collignon, Noel,Savignac, Philippe
, p. 4131 - 4143 (2007/10/03)
α-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkylphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, catalyti
