69452-53-5Relevant 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.
Abnormal Ring Opening of 1,2-Epoxyalkyldiphenylphosphine Oxides with Lithium Aluminum Hydride to Form 2-Hydroxyalkyldiphenylphosphine Oxides
Imoto, Hiroyuki,Yamashita, Mitsuji
, p. 323 - 325 (2007/10/02)
Ring opening of 1,2-epoxyalkyldiphenylphosphine oxides with LiAlH4 gives 2-hydroxyalkyldiphenylphosphine oxides in good yield.This is the first example of ring opening of 1,2-epoxyalkyldiphenylphosphine oxides to give the corresponding 2-hydroxy derivativ
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.
