16404-66-3Relevant articles and documents
Singlet oxygen generation from H2O2/MoO42-: Peroxidation of hydrophobic substrates in pure organic solvents
Nardello, Véronique,Bogaert, Stéphane,Alsters, Paul L,Aubry, Jean-Marie
, p. 8731 - 8734 (2002)
Seventeen organic solvents are screened as reaction media to conduct the molybdate-catalyzed disproportionation of hydrogen peroxide into singlet molecular oxygen, 1O2 (1Δg). The solvents are investigated by resorting to the detection of the infra-red luminescence of 1O2 at 1270 nm. Preparative peroxidations of representative substrates are carried out in the most efficient ones. The latter are protic and polar and constitute a simpler alternative to the well suited but more intricate microemulsion systems for the peroxidation of hydrophobic substrates with chemically generated 1O2.
PhSeBr mediated hydroxylative oxidative dearomatization of naphthols-an open air facile one-pot synthesis of ketols
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri,Giri, Santanab
, p. 26886 - 26894 (2016)
A new methodology for oxidative-dearomatization of planar phenols is described. An economic, viable one-pot metal free protocol for direct conversion of naphthols to α-ketols is reported. Naphthols were found to undergo facile unprecedented oxidative dearomatization with regioselective hydroxylation with phenyl selenyl bromide in open air conditions. Quaternary stereocenters were developed along with formation of sterically demanding α- and γ-ketols with high yields. Functional group tolerance like esters is revealed. A thorough study of the stereoelectronic demands of the unusual oxy-selenium reactive intermediate involved in dearomatization of 1- and 2-naphthols is carried out. 4-Hydroxy cyclohexadieneone and cyclohexadieneone aryl ethers were generated from dialkyl-phenols under similar reaction conditions providing direct evidence of the mechanical postulate. The first instance of the phenoxy-selenium interaction leading to facile dearomatization of arenes is highlighted in this manuscript.
Organophotocatalytic Aerobic Oxygenation of Phenols in a Visible-Light Continuous-Flow Photoreactor
Wellauer, Jo?l,Miladinov, Dragan,Buchholz, Thomas,Schütz, Jan,Stemmler, René T.,Medlock, Jonathan A.,Bonrath, Werner,Sparr, Christof
supporting information, p. 9748 - 9752 (2021/05/27)
A mild photocatalytic phenol oxygenation enabled by a continuous-flow photoreactor using visible light and pressurized air is described herein. Products for wide-ranging applications, including the synthesis of vitamins, were obtained in high yields by precisely controlling principal process parameters. The reactor design permits low organophotocatalyst loadings to generate singlet oxygen. It is anticipated that the efficient aerobic phenol oxygenation to benzoquinones and p-quinols contributes to sustainable synthesis.
Reductive Aromatization of Quinols with B2pin2 as Deoxidizing Agent
Liu, Bin,Xu, Yin,Luo, Zhibin,Xie, Jimin
supporting information, p. 1022 - 1024 (2020/03/19)
We have demonstrated B2pin2 as superior deoxidizing agent for the reductive deoxygenation of quinol derivatives under basic conditions. A wide range of highly functionalized phenols were obtained in good yields including a complex drug molecule, which revealed the high functional group tolerance of this protocol.
“Dark” Singlet Oxygen Made Easy
Elsherbini, Mohamed,Allemann, Rudolf K.,Wirth, Thomas
supporting information, p. 12486 - 12490 (2019/08/26)
An operationally simple continuous flow generator of “dark” singlet oxygen has been developed. The singlet oxygen was efficiently reacted with several chemical traps to give the corresponding oxygenated products in high yields. The developed “dark” singlet oxygen generator has been successfully applied in the synthesis of the antimalarial drug artemisinin.