Pyrenediones as versatile photocatalysts for oxygenation reactions with in situ generation of hydrogen peroxide under visible light

Pyrenediones (PYDs) are efficient photocatalysts for three oxygenation reactions: epoxidation of electron deficient olefins, oxidative hydroxylation of organoborons, and oxidation of sulfides via in situ generation of H2O2 under visible light irradiation, using oxygen as a terminal oxidant and IPA as a solvent and a hydrogen donor.

[1]  Tian-Le Xu,et al.  Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells. , 2018, Angewandte Chemie.

[2]  M. Antonietti,et al.  Photoredox Catalytic Organic Transformations using Heterogeneous Carbon Nitrides. , 2018, Angewandte Chemie.

[3]  B. Zhang,et al.  Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide. , 2018, Organic letters.

[4]  M. Costas,et al.  The Quest for Selectivity in Hydrogen Atom Transfer Based Aliphatic C-H Bond Oxygenation. , 2018, Accounts of chemical research.

[5]  Li‐Zhu Wu,et al.  Eosin Y as a Direct Hydrogen-Atom Transfer Photocatalyst for the Functionalization of C-H Bonds. , 2018, Angewandte Chemie.

[6]  A. Hajra,et al.  Visible light induced tetramethylethylenediamine assisted formylation of imidazopyridines. , 2018, Organic & biomolecular chemistry.

[7]  Suhua Wang,et al.  Selective detection and quantification of tryptophan and cysteine with pyrenedione as a turn-on fluorescent probe , 2018 .

[8]  Jonathan Z. Bloh,et al.  Selective Activation of C−H Bonds in a Cascade Process Combining Photochemistry and Biocatalysis , 2017, Angewandte Chemie.

[9]  H. Mayr,et al.  Solvation Accounts for the Counterintuitive Nucleophilicity Ordering of Peroxide Anions. , 2017, Angewandte Chemie.

[10]  Y. Nosaka,et al.  Generation and Detection of Reactive Oxygen Species in Photocatalysis. , 2017, Chemical reviews.

[11]  N. Jiao,et al.  Oxygenation via C-H/C-C Bond Activation with Molecular Oxygen. , 2017, Accounts of chemical research.

[12]  David A. Nicewicz,et al.  Organic Photoredox Catalysis. , 2016, Chemical reviews.

[13]  Xiaodong Chen,et al.  Cooperative photoredox catalysis. , 2016, Chemical Society reviews.

[14]  Bingbing Tian,et al.  Visible-Light Photocatalysis of Aerobic Oxidation Reactions Using Carbazolic Conjugated Microporous Polymers , 2016 .

[15]  A. Ghogare,et al.  Using Singlet Oxygen to Synthesize Natural Products and Drugs. , 2016, Chemical reviews.

[16]  T. Miura,et al.  Aerobic Photooxidative Synthesis of Phenols from Arylboronic Acids Using 2-Propanol as Solvent , 2014 .

[17]  Chuncheng Chen,et al.  Selective aerobic oxidation mediated by TiO(2) photocatalysis. , 2014, Accounts of chemical research.

[18]  Qi Yang,et al.  A simple metal-free catalytic sulfoxidation under visible light and air , 2013 .

[19]  A. Galano,et al.  Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions. , 2013, Organic & biomolecular chemistry.

[20]  T. Miura,et al.  Efficient generation of hydrogen peroxide by aerobic photooxidation of 2-propanol using anthraquinone-2-carboxylic acid and one-pot epoxidation of α,β-unsaturated ketones , 2013 .

[21]  Davide Ravelli,et al.  Photoorganocatalysis. What for? , 2013, Chemical Society reviews.

[22]  N. Jiao,et al.  Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant. , 2012, Chemical Society reviews.

[23]  M. Bancirova Sodium azide as a specific quencher of singlet oxygen during chemiluminescent detection by luminol and Cypridina luciferin analogues. , 2011, Luminescence : the journal of biological and chemical luminescence.

[24]  T. Miura,et al.  Efficient synthesis of gem-dihydroperoxides with molecular oxygen and anthraquinone under visible light irradiation with fluorescent lamp , 2011 .

[25]  K. Yoshizawa,et al.  Mechanistic Study on the Production of Hydrogen Peroxide in the Anthraquinone Process , 2011 .

[26]  K. Ohkubo,et al.  Metal-free oxygenation of cyclohexane with oxygen catalyzed by 9-mesityl-10-methylacridinium and hydrogen chloride under visible light irradiation. , 2011, Chemical communications.

[27]  T. Miura,et al.  An Efficient Synthesis of gem-Dihydroperoxides with Molecular Oxygen and Anthracene under Light Irradiation , 2010 .

[28]  T. Fujihara,et al.  Synthesis and Phase Structures of Novel π‐Acceptor Discotic Liquid Crystalline Compounds Having a Pyrenedione Core , 2008 .

[29]  Xiaobo Ji,et al.  Electrode Kinetic Studies of the Hydroquinone−Benzoquinone System and the Reaction between Hydroquinone and Ammonia in Propylene Carbonate: Application to the Indirect Electroanalytical Sensing of Ammonia , 2007 .

[30]  J. Fierro,et al.  Hydrogen peroxide synthesis: an outlook beyond the anthraquinone process. , 2006, Angewandte Chemie.

[31]  J. Iqbal,et al.  Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen. , 2005, Chemical reviews.

[32]  R. Sheldon,et al.  The Baeyer-Villiger reaction: new developments toward greener procedures. , 2004, Chemical reviews.

[33]  R. Becker,et al.  Comprehensive absorption, photophysical/chemical, and theoretical study of 2-5-ring aromatic hydrocarbon diones , 1993 .