125172-85-2Relevant academic research and scientific papers
TiO2/Cu2O nanoparticle-catalyzed direct C(sp)-P bond formation: Via aerobic oxidative coupling in air and visible light
Hosseini-Sarvari, Mona,Jafari, Fattaneh
, p. 3001 - 3006 (2020)
The synthesis of organophosphorus compounds is one of the important goals in organic chemistry. Among these compounds, alkynylphosphonates are significantly utilized as the main precursors for the synthesis of biologically active molecules in medicinal chemistry and have attracted extensive interest in the past few decades. Although few efforts have been made towards the direct and atom-economical synthesis of alkynylphosphonates, efforts towards the utilization of visible light as a green and renewable energy source have not been made to date. Here, we have promoted a strategy to construct a type of nano metal oxide composite photocatalyst (Cu2O decorated on TiO2) for the synthesis of alkynylphosphonates via direct C-P bond formation between terminal alkyne and H-phosphonate under visible light irradiation. In this p-n heterojunction photocatalyst, Cu2O acted as a visible-light absorber; moreover, the CB (conduction band) of TiO2 was favorable for accepting a photogenerated electron, and the generated electron hole (e-/h+) pair could initiate the reaction. The present study can provide a new way for the synthesis of this important class of phosphorus organic compounds.
Selective P?C(sp3) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis
Jia, Kunfang,Li, Junzhao,Chen, Yiyun
supporting information, p. 3174 - 3177 (2018/02/09)
Herein the first P?C(sp3) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P?C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.
Alkynyliodonium Salts as Alkynylating Reagents: Direct Conversion of Alkynylphenyliodonium Tosylates to Dialkyl Alkynylphosphonates with Trialkyl Phosphites
Lodaya, Jayant S.,Koser, Gerald F.
, p. 1513 - 1516 (2007/10/02)
The treatment of various alkynyl(phenyl)iodonium tosylates 1 (R = t-Bu, s-Bu, i-Pr, cyclopentyl, Ph, and p-MeC6H4; X(-) = OTs(-)) with neat trimethyl phosphite gave the dimethyl alkynylphosphonates 4a and 4d-h in isolated yields ranging from 34 to 90percent.Similar treatment of 1 (R = t-Bu, X(-) = OTs(-)) with neat triethyl and triisopropyl phosphites gave the diethyl and diisopropyl alkynylphosphonates 4b (81percent) and 4c (58percent).The byproducts of these reactions are alkyl tosylates and iodobenzene.The high yields of iodobenzene, determined by GC analysis for the reactions of 1 (R = s-Bu, p-tolyl; X(-) = OTs(-)) with trimethyl phosphite, indicate that the cleavage of the alkynyl(phenyl)iodonium ions with trialkyl phosphites proceeds with high regioselectivity at the alkynyl ligand.
