Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

doi:10.1002/anie.201906381

This content will become publicly available on August 1, 2020

Title: Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

Authors:

Huang, He ^[1]; Strater, Zack M. ^[2]; Rauch, Michael ^[2]; Shee, James ^[2]; Sisto, Thomas J. ^[2]; Nuckolls, Colin ^[2];

^[3]

Department of Chemistry and Chemical Biology, Cornell University, Ithaca NY 14853 USA
Department of Chemistry, Columbia University, New York NY 10027 USA
Department of Chemistry and Chemical Biology, Cornell University, Ithaca NY 14853 USA, Department of Chemistry, Columbia University, New York NY 10027 USA

Publication Date:: 2019-08-02

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

OSTI Identifier:: 1546103

Grant/Contract Number:: SC001944

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition) Journal Volume: 58 Journal Issue: 38; Journal ID: ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, and Lambert, Tristan H. Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication.  Germany: N. p., 2019. 
        Web.  doi:10.1002/anie.201906381.

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                    Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, & Lambert, Tristan H. Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication.  Germany.  doi:10.1002/anie.201906381.

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                    Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, and Lambert, Tristan H. Fri .  
        "Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication".  Germany.  doi:10.1002/anie.201906381.

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@article{osti_1546103,

  title        = {Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication},

  author       = {Huang, He and Strater, Zack M. and Rauch, Michael and Shee, James and Sisto, Thomas J. and Nuckolls, Colin and Lambert, Tristan H.},

  abstractNote = {},

  doi          = {10.1002/anie.201906381},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 38,

  volume       = 58,

  place        = {Germany},

  year         = {2019},

  month        = {8}

}

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DOI: 10.1002/anie.201906381

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Works referenced in this record:

Solar Synthesis: Prospects in Visible Light Photocatalysis
journal, February 2014

Schultz, D. M.; Yoon, T. P.
Science, Vol. 343, Issue 6174
DOI: 10.1126/science.1239176

Phenothiazine Radical Cation Excited States as Super-oxidants for Energy-Demanding Reactions
journal, March 2018

Christensen, Joseph A.; Phelan, Brian T.; Chaudhuri, Subhajyoti
Journal of the American Chemical Society, Vol. 140, Issue 15
DOI: 10.1021/jacs.8b01778

Organic Photoredox Catalysis
journal, June 2016

Romero, Nathan A.; Nicewicz, David A.
Chemical Reviews, Vol. 116, Issue 17
DOI: 10.1021/acs.chemrev.6b00057

Accurate Oxidation Potentials of Benzene and Biphenyl Derivatives via Electron-Transfer Equilibria and Transient Kinetics
journal, August 2009

Merkel, Paul B.; Luo, Pu; Dinnocenzo, Joseph P.
The Journal of Organic Chemistry, Vol. 74, Issue 15
DOI: 10.1021/jo9011267

Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates
journal, February 2019

Yan, Hong; Hou, Zhong-Wei; Xu, Hai-Chao
Angewandte Chemie International Edition, Vol. 58, Issue 14
DOI: 10.1002/anie.201814488

Catalysis of Radical Reactions: A Radical Chemistry Perspective
journal, October 2015

Studer, Armido; Curran, Dennis P.
Angewandte Chemie International Edition, Vol. 55, Issue 1
DOI: 10.1002/anie.201505090

Tris (dimethylamino)-cyclopropenium radical dication
journal, January 1971

Gerson, F.; Plattner, G.; Yoshida, Z.
Molecular Physics, Vol. 21, Issue 6
DOI: 10.1080/00268977100102181

Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts
journal, August 2011

Ohkubo, Kei; Kobayashi, Takaki; Fukuzumi, Shunichi
Angewandte Chemie, Vol. 123, Issue 37
DOI: 10.1002/ange.201102931

Merging Photochemistry with Electrochemistry: Functional‐Group Tolerant Electrochemical Amination of C(sp ³ )−H Bonds
journal, February 2019

Wang, Fei; Stahl, Shannon S.
Angewandte Chemie, Vol. 131, Issue 19
DOI: 10.1002/ange.201813960

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals
journal, March 2017

Silvi, Mattia; Verrier, Charlie; Rey, Yannick P.
Nature Chemistry, Vol. 9, Issue 9
DOI: 10.1038/nchem.2748

Redox catalysis in organic electrosynthesis: basic principles and recent developments
journal, January 2014

Francke, Robert; Little, R. Daniel
Chemical Society Reviews, Vol. 43, Issue 8
DOI: 10.1039/c3cs60464k

Modern Strategies in Electroorganic Synthesis
journal, July 2008

Yoshida, Jun-ichi; Kataoka, Kazuhide; Horcajada, Roberto
Chemical Reviews, Vol. 108, Issue 7
DOI: 10.1021/cr0680843

SOMO–HOMO Level Inversion in Biologically Important Radicals
journal, December 2017

Kumar, Anil; Sevilla, Michael D.
The Journal of Physical Chemistry B, Vol. 122, Issue 1
DOI: 10.1021/acs.jpcb.7b10002

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance
journal, October 2017

Yan, Ming; Kawamata, Yu; Baran, Phil S.
Chemical Reviews, Vol. 117, Issue 21
DOI: 10.1021/acs.chemrev.7b00397

Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp ³ )−H Bonds
journal, March 2019

Wang, Fei; Stahl, Shannon S.
Angewandte Chemie International Edition, Vol. 58, Issue 19
DOI: 10.1002/anie.201813960

Synthesis and reactions of porphine-type metal complexes. 15. Carbon-carbon bond formation by light assisted B12-catalysis. Nucleophilic acylation of Michael olefins
journal, November 1983

Scheffold, Rolf; Orlinski, Ryszard
Journal of the American Chemical Society, Vol. 105, Issue 24
DOI: 10.1021/ja00362a047

Visible-Light-Induced Oxygenation of Benzene by the Triplet Excited State of 2,3-Dichloro-5,6-dicyano- p -benzoquinone
journal, March 2013

Ohkubo, Kei; Fujimoto, Atsushi; Fukuzumi, Shunichi
Journal of the American Chemical Society, Vol. 135, Issue 14
DOI: 10.1021/ja402303k

Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides
journal, March 2011

Cho, Dae Won; Yoon, Ung Chan; Mariano, Patrick S.
Accounts of Chemical Research, Vol. 44, Issue 3
DOI: 10.1021/ar100125j

Cyclopropenium Salts as Cyclable, High-Potential Catholytes in Nonaqueous Media
journal, November 2016

Sevov, Christo S.; Samaroo, Sharmila K.; Sanford, Melanie S.
Advanced Energy Materials, Vol. 7, Issue 5
DOI: 10.1002/aenm.201602027

Katalyse von Radikalreaktionen: Konzepte aus Sicht der Radikalchemie
journal, October 2015

Studer, Armido; Curran, Dennis P.
Angewandte Chemie, Vol. 128, Issue 1
DOI: 10.1002/ange.201505090

Synthetic Applications of Anodic Electrochemistry
journal, December 2000

Moeller, Kevin D.
Tetrahedron, Vol. 56, Issue 49
DOI: 10.1016/S0040-4020(00)00840-1

Photoelectrocatalytic arene C–H amination
journal, February 2019

Zhang, Lei; Liardet, Laurent; Luo, Jingshan
Nature Catalysis, Vol. 2, Issue 4
DOI: 10.1038/s41929-019-0231-9

Stable radical dications
journal, January 1975

Weiss, Robert; Schloter, Klaus
Tetrahedron Letters, Vol. 16, Issue 40
DOI: 10.1016/S0040-4039(00)91392-3

Site-selective arene C-H amination via photoredox catalysis
journal, September 2015

Romero, N. A.; Margrey, K. A.; Tay, N. E.
Science, Vol. 349, Issue 6254
DOI: 10.1126/science.aac9895

Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts
journal, August 2011

Ohkubo, Kei; Kobayashi, Takaki; Fukuzumi, Shunichi
Angewandte Chemie International Edition, Vol. 50, Issue 37
DOI: 10.1002/anie.201102931

Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates
journal, January 2019

Yan, Hong; Hou, Zhong‐Wei; Xu, Hai‐Chao
Angewandte Chemie, Vol. 131, Issue 14
DOI: 10.1002/ange.201814488

Photo-induced oxidant-free oxidative C–H/N–H cross-coupling between arenes and azoles
journal, February 2017

Niu, Linbin; Yi, Hong; Wang, Shengchun
Nature Communications, Vol. 8, Issue 1
DOI: 10.1038/ncomms14226

Electrochemistry of heterosubstituted cyclopropenyl cations
journal, February 1976

Johnson, Richard W.
Tetrahedron Letters, Vol. 17, Issue 8
DOI: 10.1016/S0040-4039(00)77918-4

Photoredox Catalysis in Organic Chemistry
journal, June 2016

Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C.
The Journal of Organic Chemistry, Vol. 81, Issue 16
DOI: 10.1021/acs.joc.6b01449

Visible light photoredox catalysis: applications in organic synthesis
journal, January 2011

Narayanam, Jagan M. R.; Stephenson, Corey R. J.
Chem. Soc. Rev., Vol. 40, Issue 1
DOI: 10.1039/B913880N

Aminocyclopropenium Ions: Synthesis, Properties, and Applications
journal, August 2013

Bandar, Jeffrey; Lambert, Tristan
Synthesis, Vol. 45, Issue 18
DOI: 10.1055/s-0033-1338516

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Similar Records

This content will become publicly available on August 1, 2020

Title: Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

Citation Formats

Solar Synthesis: Prospects in Visible Light Photocatalysis journal, February 2014

Phenothiazine Radical Cation Excited States as Super-oxidants for Energy-Demanding Reactions journal, March 2018

Organic Photoredox Catalysis journal, June 2016

Accurate Oxidation Potentials of Benzene and Biphenyl Derivatives via Electron-Transfer Equilibria and Transient Kinetics journal, August 2009

Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates journal, February 2019

Catalysis of Radical Reactions: A Radical Chemistry Perspective journal, October 2015

Tris (dimethylamino)-cyclopropenium radical dication journal, January 1971

Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts journal, August 2011

Merging Photochemistry with Electrochemistry: Functional‐Group Tolerant Electrochemical Amination of C(sp 3 )−H Bonds journal, February 2019

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals journal, March 2017

Redox catalysis in organic electrosynthesis: basic principles and recent developments journal, January 2014

Modern Strategies in Electroorganic Synthesis journal, July 2008

SOMO–HOMO Level Inversion in Biologically Important Radicals journal, December 2017

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance journal, October 2017

Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp 3 )−H Bonds journal, March 2019

Synthesis and reactions of porphine-type metal complexes. 15. Carbon-carbon bond formation by light assisted B12-catalysis. Nucleophilic acylation of Michael olefins journal, November 1983

Visible-Light-Induced Oxygenation of Benzene by the Triplet Excited State of 2,3-Dichloro-5,6-dicyano- p -benzoquinone journal, March 2013

Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides journal, March 2011

Cyclopropenium Salts as Cyclable, High-Potential Catholytes in Nonaqueous Media journal, November 2016

Katalyse von Radikalreaktionen: Konzepte aus Sicht der Radikalchemie journal, October 2015

Synthetic Applications of Anodic Electrochemistry journal, December 2000

Photoelectrocatalytic arene C–H amination journal, February 2019

Stable radical dications journal, January 1975

Site-selective arene C-H amination via photoredox catalysis journal, September 2015

Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts journal, August 2011

Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates journal, January 2019

Photo-induced oxidant-free oxidative C–H/N–H cross-coupling between arenes and azoles journal, February 2017

Electrochemistry of heterosubstituted cyclopropenyl cations journal, February 1976

Photoredox Catalysis in Organic Chemistry journal, June 2016

Visible light photoredox catalysis: applications in organic synthesis journal, January 2011

Aminocyclopropenium Ions: Synthesis, Properties, and Applications journal, August 2013

Solar Synthesis: Prospects in Visible Light Photocatalysis
journal, February 2014

Phenothiazine Radical Cation Excited States as Super-oxidants for Energy-Demanding Reactions
journal, March 2018

Organic Photoredox Catalysis
journal, June 2016

Accurate Oxidation Potentials of Benzene and Biphenyl Derivatives via Electron-Transfer Equilibria and Transient Kinetics
journal, August 2009

Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates
journal, February 2019

Catalysis of Radical Reactions: A Radical Chemistry Perspective
journal, October 2015

Tris (dimethylamino)-cyclopropenium radical dication
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Direct Oxygenation of Benzene to Phenol Using Quinolinium Ions as Homogeneous Photocatalysts
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Merging Photochemistry with Electrochemistry: Functional‐Group Tolerant Electrochemical Amination of C(sp ³ )−H Bonds
journal, February 2019

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals
journal, March 2017

Redox catalysis in organic electrosynthesis: basic principles and recent developments
journal, January 2014

Modern Strategies in Electroorganic Synthesis
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Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp ³ )−H Bonds
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Visible-Light-Induced Oxygenation of Benzene by the Triplet Excited State of 2,3-Dichloro-5,6-dicyano- p -benzoquinone
journal, March 2013

Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides
journal, March 2011

Cyclopropenium Salts as Cyclable, High-Potential Catholytes in Nonaqueous Media
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Site-selective arene C-H amination via photoredox catalysis
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