Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Du, Ya; Pearson, Ryan M.; Lim, Chern-Hooi; Sartor, Steven M.; Ryan, Matthew D.; Yang, Haishen; Damrauer, Niels H.; Miyake, Garret M.

doi:10.1002/chem.201702926

Title: Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Journal Article · Tue Jun 27 00:00:00 EDT 2017 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201702926· OSTI ID:1533143

Du, Ya ^[1]; Pearson, Ryan M. ^[1];

^[1]; Sartor, Steven M. ^[1]; Ryan, Matthew D. ^[1]; Yang, Haishen ^[2]; Damrauer, Niels H. ^[1];

^[1]

Univ. of Colorado, Boulder, CO (United States)
Univ. of Colorado, Boulder, CO (United States); Shanghai University of Electric Power (China)

Abstract Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible‐light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible‐light PCs for trifluoromethylation reactions and dual photoredox/nickel‐catalyzed C−N and C−S cross‐coupling reactions, both of which have been historically exclusive to precious metal PCs.

View Accepted Manuscript (DOE)

View Accepted Manuscript (Publisher)

Cite

Export

Save

Research Organization:: Univ. of Colorado, Boulder, CO (United States)

Sponsoring Organization:: USDOE Advanced Research Projects Agency - Energy (ARPA-E)

Grant/Contract Number:: AR0000683

OSTI ID:: 1533143

Alternate ID(s):: OSTI ID: 1375468

Journal Information:: Chemistry - A European Journal, Vol. 23, Issue 46; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 172 works

Citation information provided by
Web of Science

References (81)

Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II) Welin, Eric R.; Le, Chip; Arias-Rotondo, Daniela M. Science, Vol. 355, Issue 6323 https://doi.org/10.1126/science.aal2490	journal	January 2017
Solar Synthesis: Prospects in Visible Light Photocatalysis Schultz, D. M.; Yoon, T. P. Science, Vol. 343, Issue 6174 https://doi.org/10.1126/science.1239176	journal	February 2014
Photocatalytic Oxygenation of Anthracenes and Olefins with Dioxygen via Selective Radical Coupling Using 9-Mesityl-10-methylacridinium Ion as an Effective Electron-Transfer Photocatalyst Kotani, Hiroaki; Ohkubo, Kei; Fukuzumi, Shunichi Journal of the American Chemical Society, Vol. 126, Issue 49 https://doi.org/10.1021/ja048353b	journal	December 2004
Organic Photoredox Catalysis Romero, Nathan A.; Nicewicz, David A. Chemical Reviews, Vol. 116, Issue 17 https://doi.org/10.1021/acs.chemrev.6b00057	journal	June 2016
Chemoselective Radical Dehalogenation and C–C Bond Formation on Aryl Halide Substrates Using Organic Photoredox Catalysts Poelma, Saemi O.; Burnett, G. Leslie; Discekici, Emre H. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01034	journal	June 2016
Uncovering the Roles of Oxygen in Cr(III) Photoredox Catalysis Higgins, Robert F.; Fatur, Steven M.; Shepard, Samuel G. Journal of the American Chemical Society, Vol. 138, Issue 16 https://doi.org/10.1021/jacs.6b02723	journal	January 2016
Metal-Free Atom Transfer Radical Polymerization Treat, Nicolas J.; Sprafke, Hazel; Kramer, John W. Journal of the American Chemical Society, Vol. 136, Issue 45 https://doi.org/10.1021/ja510389m	journal	October 2014
New Ambipolar Organic Semiconductors. 1. Synthesis, Single-Crystal Structures, Redox Properties, and Photophysics of Phenoxazine-Based Donor−Acceptor Molecules Zhu, Yan; Kulkarni, Abhishek P.; Wu, Pei-Tzu Chemistry of Materials, Vol. 20, Issue 13 https://doi.org/10.1021/cm702212w	journal	July 2008
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C. Chemical Reviews, Vol. 113, Issue 7 https://doi.org/10.1021/cr300503r	journal	March 2013
Ruthenium complexes as antimicrobial agents Li, Fangfei; Collins, J. Grant; Keene, F. Richard Chemical Society Reviews, Vol. 44, Issue 8 https://doi.org/10.1039/C4CS00343H	journal	January 2015
Organocatalyzed Atom Transfer Radical Polymerization: Perspectives on Catalyst Design and Performance Theriot, Jordan C.; McCarthy, Blaine G.; Lim, Chern-Hooi Macromolecular Rapid Communications, Vol. 38, Issue 13 https://doi.org/10.1002/marc.201700040	journal	April 2017
Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts Wallentin, Carl-Johan; Nguyen, John D.; Finkbeiner, Peter Journal of the American Chemical Society, Vol. 134, Issue 21 https://doi.org/10.1021/ja300798k	journal	May 2012
Solvent effects on the intramolecular charge transfer character of N , N -diaryl dihydrophenazine catalysts for organocatalyzed atom transfer radical polymerization Ryan, Matthew D.; Theriot, Jordan C.; Lim, Chern-Hooi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 55, Issue 18 https://doi.org/10.1002/pola.28574	journal	March 2017
Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides Oderinde, Martins S.; Jones, Natalie H.; Juneau, Antoine Angewandte Chemie, Vol. 128, Issue 42 https://doi.org/10.1002/ange.201604429	journal	October 2016
Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles Shaw, M. H.; Shurtleff, V. W.; Terrett, J. A. Science, Vol. 352, Issue 6291 https://doi.org/10.1126/science.aaf6635	journal	April 2016
Photocatalysis in organic and polymer synthesis Corrigan, Nathaniel; Shanmugam, Sivaprakash; Xu, Jiangtao Chemical Society Reviews, Vol. 45, Issue 22 https://doi.org/10.1039/C6CS00185H	journal	January 2016
Organocatalyzed Atom Transfer Radical Polymerization Using N -Aryl Phenoxazines as Photoredox Catalysts Pearson, Ryan M.; Lim, Chern-Hooi; McCarthy, Blaine G. Journal of the American Chemical Society, Vol. 138, Issue 35 https://doi.org/10.1021/jacs.6b08068	journal	August 2016
Outer-sphere dissociative electron transfer to organic molecules: a source of radicals or carbanions? Direct and indirect electrochemistry of perfluoroalkyl bromides and iodides Andrieux, Claude P.; Gelis, Laurence; Medebielle, Maurice Journal of the American Chemical Society, Vol. 112, Issue 9 https://doi.org/10.1021/ja00165a040	journal	April 1990
Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism Meyer, Andreas Uwe; Straková, Karolína; Slanina, Tomáš Chemistry - A European Journal, Vol. 22, Issue 25 https://doi.org/10.1002/chem.201601000	journal	May 2016
Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides Noble, Adam; McCarver, Stefan J.; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 137, Issue 2 https://doi.org/10.1021/ja511913h	journal	January 2015
Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates Jouffroy, Matthieu; Primer, David N.; Molander, Gary A. Journal of the American Chemical Society, Vol. 138, Issue 2 https://doi.org/10.1021/jacs.5b10963	journal	December 2015
Light-Controlled Radical Polymerization: Mechanisms, Methods, and Applications Chen, Mao; Zhong, Mingjiang; Johnson, Jeremiah A. Chemical Reviews, Vol. 116, Issue 17 https://doi.org/10.1021/acs.chemrev.5b00671	journal	March 2016
A General Approach to Catalytic Alkene Anti-Markovnikov Hydrofunctionalization Reactions via Acridinium Photoredox Catalysis Margrey, Kaila A.; Nicewicz, David A. Accounts of Chemical Research, Vol. 49, Issue 9 https://doi.org/10.1021/acs.accounts.6b00304	journal	September 2016
Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis Tellis, J. C.; Primer, D. N.; Molander, G. A. Science, Vol. 345, Issue 6195 https://doi.org/10.1126/science.1253647	journal	June 2014
Excited-state properties of a triply ortho-metalated iridium(III) complex King, K. A.; Spellane, P. J.; Watts, Richard J. Journal of the American Chemical Society, Vol. 107, Issue 5 https://doi.org/10.1021/ja00291a064	journal	March 1985
Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis Joshi-Pangu, Amruta; Lévesque, François; Roth, Hudson G. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01240	journal	June 2016
Trifluoromethylation by Visible-Light-Driven Photoredox Catalysis Koike, Takashi; Akita, Munetaka Topics in Catalysis, Vol. 57, Issue 10-13 https://doi.org/10.1007/s11244-014-0259-7	journal	March 2014
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds Miyaura, Norio.; Suzuki, Akira. Chemical Reviews, Vol. 95, Issue 7 https://doi.org/10.1021/cr00039a007	journal	November 1995
Shining Light on Photoredox Catalysis: Theory and Synthetic Applications Tucker, Joseph W.; Stephenson, Corey R. J. The Journal of Organic Chemistry, Vol. 77, Issue 4 https://doi.org/10.1021/jo202538x	journal	January 2012
Redesign of a Pyrylium Photoredox Catalyst and Its Application to the Generation of Carbonyl Ylides Alfonzo, Edwin; Alfonso, Felix Steven; Beeler, Aaron B. Organic Letters, Vol. 19, Issue 11 https://doi.org/10.1021/acs.orglett.7b01222	journal	May 2017
Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes Lamansky, Sergey; Djurovich, Peter; Murphy, Drew Inorganic Chemistry, Vol. 40, Issue 7 https://doi.org/10.1021/ic0008969	journal	March 2001
Photochemistry and Photophysics of Coordination Compounds: Iridium Flamigni, Lucia; Barbieri, Andrea; Sabatini, Cristiana Photochemistry and Photophysics of Coordination Compounds II https://doi.org/10.1007/128_2007_131	book	January 2007
A highly reducing metal-free photoredox catalyst: design and application in radical dehalogenations Discekici, Emre H.; Treat, Nicolas J.; Poelma, Saemi O. Chemical Communications, Vol. 51, Issue 58 https://doi.org/10.1039/C5CC04677G	journal	January 2015
Aryl amination using ligand-free Ni(II) salts and photoredox catalysis Corcoran, Emily B.; Pirnot, Michael T.; Lin, Shishi Science, Vol. 353, Issue 6296 https://doi.org/10.1126/science.aag0209	journal	June 2016
Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions Molnár, Árpád Chemical Reviews, Vol. 111, Issue 3 https://doi.org/10.1021/cr100355b	journal	March 2011
Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides Oderinde, Martins S.; Jones, Natalie H.; Juneau, Antoine Angewandte Chemie International Edition, Vol. 55, Issue 42 https://doi.org/10.1002/anie.201604429	journal	October 2016
Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts Nguyen, John D.; Tucker, Joseph W.; Konieczynska, Marlena D. Journal of the American Chemical Society, Vol. 133, Issue 12 https://doi.org/10.1021/ja108560e	journal	March 2011
A Stable Radical-Substituted Radical Cation with Strongly Ferromagnetic Interaction: Nitronyl Nitroxide-Substituted 5,10-Diphenyl-5,10-dihydrophenazine Radical Cation Hiraoka, Shinsuke; Okamoto, Toshihiro; Kozaki, Masatoshi Journal of the American Chemical Society, Vol. 126, Issue 1 https://doi.org/10.1021/ja0367748	journal	January 2004
Photoredox Catalysis in Organic Chemistry Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01449	journal	June 2016
Direct C(sp ³ )–H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals Shields, Benjamin J.; Doyle, Abigail G. Journal of the American Chemical Society, Vol. 138, Issue 39 https://doi.org/10.1021/jacs.6b08397	journal	September 2016
Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S. Chemical Reviews, Vol. 111, Issue 3 https://doi.org/10.1021/cr100327p	journal	March 2011
Photoinduced Organocatalyzed Atom Transfer Radical Polymerization Using Continuous Flow Ramsey, Bonnie L.; Pearson, Ryan M.; Beck, Logan R. Macromolecules, Vol. 50, Issue 7 https://doi.org/10.1021/acs.macromol.6b02791	journal	March 2017
Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions Ruiz-Castillo, Paula; Buchwald, Stephen L. Chemical Reviews, Vol. 116, Issue 19 https://doi.org/10.1021/acs.chemrev.6b00512	journal	September 2016
Organocatalyzed atom transfer radical polymerization driven by visible light Theriot, J. C.; Lim, C. -H.; Yang, H. Science, Vol. 352, Issue 6289 https://doi.org/10.1126/science.aaf3935	journal	March 2016
Impact of Light Intensity on Control in Photoinduced Organocatalyzed Atom Transfer Radical Polymerization Ryan, Matthew D.; Pearson, Ryan M.; French, Tracy A. Macromolecules, Vol. 50, Issue 12 https://doi.org/10.1021/acs.macromol.7b00502	journal	June 2017
Highly efficient organic light-emitting diodes from delayed fluorescence Uoyama, Hiroki; Goushi, Kenichi; Shizu, Katsuyuki Nature, Vol. 492, Issue 7428 https://doi.org/10.1038/nature11687	journal	December 2012
A stable quasi-solid-state dye-sensitized solar cell with an amphiphilic ruthenium sensitizer and polymer gel electrolyte Wang, Peng; Zakeeruddin, Shaik M.; Moser, Jacques E. Nature Materials, Vol. 2, Issue 6 https://doi.org/10.1038/nmat904	journal	May 2003
Reduction of aryl halides by consecutive visible light-induced electron transfer processes Ghosh, I.; Ghosh, T.; Bardagi, J. I. Science, Vol. 346, Issue 6210 https://doi.org/10.1126/science.1258232	journal	November 2014
Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals Oderinde, Martins S.; Frenette, Mathieu; Robbins, Daniel W. Journal of the American Chemical Society, Vol. 138, Issue 6 https://doi.org/10.1021/jacs.5b11244	journal	February 2016
Switching on elusive organometallic mechanisms with photoredox catalysis Terrett, Jack A.; Cuthbertson, James D.; Shurtleff, Valerie W. Nature, Vol. 524, Issue 7565 https://doi.org/10.1038/nature14875	journal	August 2015
Organic photocatalysts for cleaner polymer synthesis Shanmugam, S.; Boyer, C. Science, Vol. 352, Issue 6289 https://doi.org/10.1126/science.aaf7465	journal	May 2016
A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO₂ films O'Regan, Brian; Grätzel, Michael Nature, Vol. 353, Issue 6346, p. 737-740 https://doi.org/10.1038/353737a0	journal	October 1991
Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds Pham, Phong V.; Nagib, David A.; MacMillan, David W. C. Angewandte Chemie, Vol. 123, Issue 27 https://doi.org/10.1002/ange.201101861	journal	May 2011
Estimation of Standard Reduction Potentials of Halogen Atoms and Alkyl Halides Isse, Abdirisak A.; Lin, Ching Yeh; Coote, Michelle L. The Journal of Physical Chemistry B, Vol. 115, Issue 4 https://doi.org/10.1021/jp109613t	journal	February 2011
Atom Transfer Radical Polymerization Matyjaszewski, Krzysztof; Xia, Jianhui Chemical Reviews, Vol. 101, Issue 9 https://doi.org/10.1021/cr940534g	journal	September 2001
Intramolecular Charge Transfer and Ion Pairing in N,N -Diaryl Dihydrophenazine Photoredox Catalysts for Efficient Organocatalyzed Atom Transfer Radical Polymerization Lim, Chern-Hooi; Ryan, Matthew D.; McCarthy, Blaine G. Journal of the American Chemical Society, Vol. 139, Issue 1 https://doi.org/10.1021/jacs.6b11022	journal	December 2016
Nearly 100% internal phosphorescence efficiency in an organic light-emitting device Adachi, Chihaya; Baldo, Marc A.; Thompson, Mark E. Journal of Applied Physics, Vol. 90, Issue 10 https://doi.org/10.1063/1.1409582	journal	November 2001
Synthetic applications of eosin Y in photoredox catalysis Hari, Durga Prasad; König, Burkhard Chem. Commun., Vol. 50, Issue 51 https://doi.org/10.1039/C4CC00751D	journal	January 2014
Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(sp ³ )–C(sp ² ) Cross-Coupling Luo, Jian; Zhang, Jian ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b02204	journal	January 2016
Metal-Free, Cooperative Asymmetric Organophotoredox Catalysis with Visible Light Neumann, Matthias; Füldner, Stefan; König, Burkhard Angewandte Chemie International Edition, Vol. 50, Issue 4 https://doi.org/10.1002/anie.201002992	journal	September 2010
Quantum dots versus organic dyes as fluorescent labels Resch-Genger, Ute; Grabolle, Markus; Cavaliere-Jaricot, Sara Nature Methods, Vol. 5, Issue 9 https://doi.org/10.1038/nmeth.1248	journal	August 2008
Estimation of excited-state redox potentials by electron-transfer quenching. Application of electron-transfer theory to excited-state redox processes Bock, C. R.; Connor, J. A.; Gutierrez, A. R. Journal of the American Chemical Society, Vol. 101, Issue 17 https://doi.org/10.1021/ja00511a007	journal	August 1979
Aqueous-Medium Carbon–Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation Yoshioka, Eito; Kohtani, Shigeru; Jichu, Takahisa The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01102	journal	June 2016
Trifluoromethylation of heterocycles via visible light photoredox catalysis Iqbal, Naeem; Choi, Sungkyu; Ko, Euna Tetrahedron Letters, Vol. 53, Issue 15 https://doi.org/10.1016/j.tetlet.2012.02.032	journal	April 2012
Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence Juris, A.; Balzani, V.; Barigelletti, F. Coordination Chemistry Reviews, Vol. 84 https://doi.org/10.1016/0010-8545(88)80032-8	journal	March 1988
Photofunctional triplet excited states of cyclometalated Ir(iii) complexes: beyond electroluminescence You, Youngmin; Nam, Wonwoo Chemical Society Reviews, Vol. 41, Issue 21 https://doi.org/10.1039/c2cs35171d	journal	January 2012
Perylene as an Organic Photocatalyst for the Radical Polymerization of Functionalized Vinyl Monomers through Oxidative Quenching with Alkyl Bromides and Visible Light Miyake, Garret M.; Theriot, Jordan C. Macromolecules, Vol. 47, Issue 23 https://doi.org/10.1021/ma502044f	journal	November 2014
Asymmetric copper-catalyzed C-N cross-couplings induced by visible light Kainz, Q. M.; Matier, C. D.; Bartoszewicz, A. Science, Vol. 351, Issue 6274 https://doi.org/10.1126/science.aad8313	journal	February 2016
Merging photoredox with nickel catalysis: Coupling of -carboxyl sp3-carbons with aryl halides Zuo, Z.; Ahneman, D. T.; Chu, L. Science, Vol. 345, Issue 6195 https://doi.org/10.1126/science.1255525	journal	June 2014
Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds Pham, Phong V.; Nagib, David A.; MacMillan, David W. C. Angewandte Chemie International Edition, Vol. 50, Issue 27 https://doi.org/10.1002/anie.201101861	journal	May 2011
Transition Metal-Catalyzed Living Radical Polymerization: Toward Perfection in Catalysis and Precision Polymer Synthesis Ouchi, Makoto; Terashima, Takaya; Sawamoto, Mitsuo Chemical Reviews, Vol. 109, Issue 11 https://doi.org/10.1021/cr900234b	journal	November 2009
The photophysics of photoredox catalysis: a roadmap for catalyst design Arias-Rotondo, Daniela M.; McCusker, James K. Chemical Society Reviews, Vol. 45, Issue 21 https://doi.org/10.1039/C6CS00526H	journal	January 2016
A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells Gill, Martin R.; Garcia-Lara, Jorge; Foster, Simon J. Nature Chemistry, Vol. 1, Issue 8 https://doi.org/10.1038/nchem.406	journal	October 2009
Chemical Redox Agents for Organometallic Chemistry Connelly, Neil G.; Geiger, William E. Chemical Reviews, Vol. 96, Issue 2 https://doi.org/10.1021/cr940053x	journal	January 1996
Metallfreie kooperative asymmetrische Organophotoredoxkatalyse mit sichtbarem Licht Neumann, Matthias; Füldner, Stefan; König, Burkhard Angewandte Chemie, Vol. 123, Issue 4 https://doi.org/10.1002/ange.201002992	journal	September 2010
Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis Rohokale, Rajendra S.; Koenig, Burkhard; Dhavale, Dilip D. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b00979	journal	June 2016
Luminescent Rhenium(I) and Iridium(III) Polypyridine Complexes as Biological Probes, Imaging Reagents, and Photocytotoxic Agents Lo, Kenneth Kam-Wing Accounts of Chemical Research, Vol. 48, Issue 12 https://doi.org/10.1021/acs.accounts.5b00211	journal	July 2015
Organocatalyzed, Photoredox Heteroarylation of 2-Trifluoroboratochromanones via C–H Functionalization Matsui, Jennifer K.; Molander, Gary A. Organic Letters, Vol. 19, Issue 4 https://doi.org/10.1021/acs.orglett.7b00196	journal	February 2017
Fragment Couplings via CO ₂ Extrusion–Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox Le, Chi “Chip”; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 137, Issue 37 https://doi.org/10.1021/jacs.5b08304	journal	September 2015
A stable quasi-solid-state dye-sensitized solar cell with an amphiphilic ruthenium sensitizer and polymer gel electrolyte Wang, Peng; Zakeeruddin, Shaik M.; Moser, Jacques E. Materials for Sustainable Energy https://doi.org/10.1142/9789814317665_0014	book	October 2010
Synthetic applications of eosin Y in photoredox catalysis Hari, Durga Prasad; König, Burkhard Universität Regensburg https://doi.org/10.5283/epub.29774	text	January 2014

Cited By (31)

Organische Photosäuren‐ und Photobasenbildner für Polymerisationen: Jüngste Fortschritte und Herausforderungen Zivic, Nicolas; Kuroishi, Paula K.; Dumur, Frédéric Angewandte Chemie, Vol. 131, Issue 31 https://doi.org/10.1002/ange.201810118	journal	April 2019
Semi‐heterogene duale Nickel‐/Photokatalyse mit Kohlenstoffnitriden: Veresterung von Carbonsäuren mit Arylhalogeniden Pieber, Bartholomäus; Malik, Jamal A.; Cavedon, Cristian Angewandte Chemie, Vol. 131, Issue 28 https://doi.org/10.1002/ange.201902785	journal	June 2019
Dimethyl Dihydroacridines as Photocatalysts in Organocatalyzed Atom Transfer Radical Polymerization of Acrylate Monomers Buss, Bonnie L.; Lim, Chern‐Hooi; Miyake, Garret M. Angewandte Chemie, Vol. 132, Issue 8 https://doi.org/10.1002/ange.201910828	journal	January 2020
Recent Advances and Challenges in the Design of Organic Photoacid and Photobase Generators for Polymerizations Zivic, Nicolas; Kuroishi, Paula K.; Dumur, Frédéric Angewandte Chemie International Edition, Vol. 58, Issue 31 https://doi.org/10.1002/anie.201810118	journal	April 2019
Semi‐heterogeneous Dual Nickel/Photocatalysis using Carbon Nitrides: Esterification of Carboxylic Acids with Aryl Halides Pieber, Bartholomäus; Malik, Jamal A.; Cavedon, Cristian Angewandte Chemie International Edition, Vol. 58, Issue 28 https://doi.org/10.1002/anie.201902785	journal	July 2019
Dimethyl Dihydroacridines as Photocatalysts in Organocatalyzed Atom Transfer Radical Polymerization of Acrylate Monomers Buss, Bonnie L.; Lim, Chern‐Hooi; Miyake, Garret M. Angewandte Chemie International Edition, Vol. 59, Issue 8 https://doi.org/10.1002/anie.201910828	journal	January 2020
Naphthochromenones: Organic Bimodal Photocatalysts Engaging in Both Oxidative and Reductive Quenching Processes Mateos, Javier; Rigodanza, Francesco; Vega‐Peñaloza, Alberto Angewandte Chemie International Edition, Vol. 59, Issue 3 https://doi.org/10.1002/anie.201912455	journal	November 2019
Visible‐Light‐Mediated Liberation and In Situ Conversion of Fluorophosgene Petzold, Daniel; Nitschke, Philipp; Brandl, Fabian Chemistry – A European Journal, Vol. 25, Issue 1 https://doi.org/10.1002/chem.201804603	journal	November 2018
Photochemical Strategies for Carbon-Heteroatom Bond Formation: Photochemical Strategies for Carbon-Heteroatom Bond Formation Cavedon, Cristian; Seeberger, Peter H.; Pieber, Bartholomäus European Journal of Organic Chemistry, Vol. 2020, Issue 10 https://doi.org/10.1002/ejoc.201901173	journal	September 2019
Selectivity control of CO versus HCOO− production in the visible-light-driven catalytic reduction of CO2 with two cooperative metal sites Guo, Zhenguo; Chen, Gui; Cometto, Claudio Nature Catalysis, Vol. 2, Issue 9 https://doi.org/10.1038/s41929-019-0331-6	journal	August 2019
Application of coumarin dyes for organic photoredox catalysis Gualandi, Andrea; Rodeghiero, Giacomo; Della Rocca, Emanuele Chemical Communications, Vol. 54, Issue 72 https://doi.org/10.1039/c8cc04048f	journal	January 2018
Photoinduced metal-free atom transfer radical polymerizations: state-of-the-art, mechanistic aspects and applications Yilmaz, Gorkem; Yagci, Yusuf Polymer Chemistry, Vol. 9, Issue 14 https://doi.org/10.1039/c8py00207j	journal	January 2018
Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones Berger, Anna Lucia; Donabauer, Karsten; König, Burkhard Chemical Science, Vol. 9, Issue 36 https://doi.org/10.1039/c8sc02038h	journal	January 2018
Single-molecule photoredox catalysis Haimerl, Josef; Ghosh, Indrajit; König, Burkhard Chemical Science, Vol. 10, Issue 3 https://doi.org/10.1039/c8sc03860k	journal	January 2019
Practical heterogeneous photoredox/nickel dual catalysis for C–N and C–O coupling reactions Liu, Yi-Yin; Liang, Dong; Lu, Liang-Qiu Chemical Communications, Vol. 55, Issue 33 https://doi.org/10.1039/c9cc00987f	journal	January 2019
Visible light promoted fluoroalkylation of alkenes and alkynes using 2-bromophenol as a catalyst Zhu, Erlin; Liu, Xiao-Xiao; Wang, An-Jun Chemical Communications, Vol. 55, Issue 81 https://doi.org/10.1039/c9cc06587c	journal	January 2019
A general and green fluoroalkylation reaction promoted via noncovalent interactions between acetone and fluoroalkyl iodides Mao, Ting; Ma, Ming-Jian; Zhao, Liang Chemical Communications, Vol. 56, Issue 12 https://doi.org/10.1039/c9cc09517a	journal	January 2020
Small-molecule activation with iron porphyrins using electrons, photons and protons: some recent advances and future strategies Anxolabéhère-Mallart, Elodie; Bonin, Julien; Fave, Claire Dalton Transactions, Vol. 48, Issue 18 https://doi.org/10.1039/c9dt00136k	journal	January 2019
Organocatalytic C–H fluoroalkylation of commodity polymers Lewis, Sally E.; Wilhelmy, Bradley E.; Leibfarth, Frank A. Polymer Chemistry, Vol. 11, Issue 30 https://doi.org/10.1039/c9py01884k	journal	January 2020
Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light Lemir, Ignacio D.; Castro-Godoy, Willber D.; Heredia, Adrián A. RSC Advances, Vol. 9, Issue 39 https://doi.org/10.1039/c9ra03642c	journal	January 2019
Reactivity control of a photocatalytic system by changing the light intensity Kerzig, Christoph; Wenger, Oliver S. Chemical Science, Vol. 10, Issue 48 https://doi.org/10.1039/c9sc04584h	journal	January 2019
Perspective: How can ultrafast laser spectroscopy inform the design of new organic photoredox catalysts for chemical and materials synthesis? Orr-Ewing, Andrew J. Structural Dynamics, Vol. 6, Issue 1 https://doi.org/10.1063/1.5082620	journal	January 2019
Photocatalytic formation of carbon–sulfur bonds Wimmer, Alexander; König, Burkhard Beilstein Journal of Organic Chemistry, Vol. 14 https://doi.org/10.3762/bjoc.14.4	journal	January 2018
Naphthochromenones: Organic Bimodal Photocatalysts Engaging in Both Oxidative and Reductive Quenching Processes Mateos, Javier; Rigodanza, Francesco; Vega‐Peñaloza, Alberto Angewandte Chemie, Vol. 132, Issue 3 https://doi.org/10.1002/ange.201912455	journal	November 2019
Titelbild: Dimethyl Dihydroacridines as Photocatalysts in Organocatalyzed Atom Transfer Radical Polymerization of Acrylate Monomers (Angew. Chem. 8/2020) Buss, Bonnie L.; Lim, Chern‐Hooi; Miyake, Garret M. Angewandte Chemie, Vol. 132, Issue 8 https://doi.org/10.1002/ange.202000293	journal	January 2020
Photocatalytic Synthesis of Polycyclic Indolones Saget, Tanguy; König, Burkhard Chemistry – A European Journal, Vol. 26, Issue 31 https://doi.org/10.1002/chem.202001324	journal	May 2020
Synthesis of star polymers using organocatalyzed atom transfer radical polymerization through a core-first approach Buss, Bonnie L.; Beck, Logan R.; Miyake, Garret M. Polymer Chemistry, Vol. 9, Issue 13 https://doi.org/10.1039/c7py01833a	journal	January 2018
Degenerative xanthate transfer to olefins under visible-light photocatalysis Kaga, Atsushi; Wu, Xiangyang; Lim, Joel Yi Jie Beilstein Journal of Organic Chemistry, Vol. 14 https://doi.org/10.3762/bjoc.14.283	journal	January 2018
Photocatalytic Synthesis of Polycyclic Indolones Saget, Tanguy; König, Burkhard Universität Regensburg https://doi.org/10.5283/epub.43127	text	January 2020
Photocatalytic formation of carbon–sulfur bonds Wimmer, Alexander; König, Burkhard Universität Regensburg https://doi.org/10.5283/epub.36490	text	January 2018
Reactivity control of a photocatalytic system by changing the light intensity Kerzig, Christoph; Wenger, Oliver S. Royal Society of Chemistry https://doi.org/10.5451/unibas-ep73729	text	January 2019

Similar Records

Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp³)–H Cross-Coupling

Journal Article · Fri Jan 29 00:00:00 EST 2021 · Accounts of Chemical Research · OSTI ID:1533143

Kariofillis, Stavros K.; Doyle, Abigail G.

Design and Evaluation of Artificial Hybrid Photoredox Biocatalysts

Journal Article · Tue Aug 04 00:00:00 EDT 2020 · ChemBioChem: a European journal of chemical biology · OSTI ID:1533143

Schwochert, Timothy D.; Cruz, Cole L.; Watters, John W.; +3 more

First use of a divalent lanthanide for visible-light-promoted photoredox catalysis

Journal Article · Mon Jan 01 00:00:00 EST 2018 · Chemical Science · OSTI ID:1533143

Jenks, Tyler C.; Bailey, Matthew D.; Hovey, Jessica L.; +5 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Chemistry

Title: Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Citation Formats

References (81)

Cited By (31)

Similar Records

Related Subjects