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

Abstract

We report the first catalytic use of a divalent lanthanide in visible-light-promoted bond-forming reactions. Our new precatalyst uses europium in the +2 oxidation state and is active in the presence of blue light from light-emitting diodes. The use of low-energy visible light reduces the occurrence of potential side reactions that might be induced by higher-energy UV light. The system described here uses zinc metal as a sacrificial reductant and is tolerant to wet, protic solvents. The catalyst can be made in situ from relatively inexpensive and air-stable EuCl 3·6H 2O, and the ligand can be synthesized in large quantities in two steps. With 0.5% loading of precatalyst, an average of 120 turnovers was observed in six hours for reductive coupling of benzyl chloride. We expect that the results will initiate the study of visible-light-promoted photoredox catalysis using divalent europium in a variety of reactions.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [1];  [1]; ORCiD logo [1]
  1. Wayne State Univ., Detroit, MI (United States)
Publication Date:
Research Org.:
Wayne State Univ., Detroit, MI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1414501
Alternate Identifier(s):
OSTI ID: 1505577
Grant/Contract Number:  
SC0012628
Resource Type:
Journal Article: Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 9; Journal Issue: 5; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Jenks, Tyler C., Bailey, Matthew D., Hovey, Jessica L., Fernando, Shanilke, Basnayake, Gihan, Cross, Michael E., Li, Wen, and Allen, Matthew J. First use of a divalent lanthanide for visible-light-promoted photoredox catalysis. United States: N. p., 2017. Web. doi:10.1039/c7sc02479g.
Jenks, Tyler C., Bailey, Matthew D., Hovey, Jessica L., Fernando, Shanilke, Basnayake, Gihan, Cross, Michael E., Li, Wen, & Allen, Matthew J. First use of a divalent lanthanide for visible-light-promoted photoredox catalysis. United States. doi:10.1039/c7sc02479g.
Jenks, Tyler C., Bailey, Matthew D., Hovey, Jessica L., Fernando, Shanilke, Basnayake, Gihan, Cross, Michael E., Li, Wen, and Allen, Matthew J. Thu . "First use of a divalent lanthanide for visible-light-promoted photoredox catalysis". United States. doi:10.1039/c7sc02479g.
@article{osti_1414501,
title = {First use of a divalent lanthanide for visible-light-promoted photoredox catalysis},
author = {Jenks, Tyler C. and Bailey, Matthew D. and Hovey, Jessica L. and Fernando, Shanilke and Basnayake, Gihan and Cross, Michael E. and Li, Wen and Allen, Matthew J.},
abstractNote = {We report the first catalytic use of a divalent lanthanide in visible-light-promoted bond-forming reactions. Our new precatalyst uses europium in the +2 oxidation state and is active in the presence of blue light from light-emitting diodes. The use of low-energy visible light reduces the occurrence of potential side reactions that might be induced by higher-energy UV light. The system described here uses zinc metal as a sacrificial reductant and is tolerant to wet, protic solvents. The catalyst can be made in situ from relatively inexpensive and air-stable EuCl3·6H2O, and the ligand can be synthesized in large quantities in two steps. With 0.5% loading of precatalyst, an average of 120 turnovers was observed in six hours for reductive coupling of benzyl chloride. We expect that the results will initiate the study of visible-light-promoted photoredox catalysis using divalent europium in a variety of reactions.},
doi = {10.1039/c7sc02479g},
journal = {Chemical Science},
issn = {2041-6520},
number = 5,
volume = 9,
place = {United States},
year = {2017},
month = {12}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at 10.1039/c7sc02479g

Citation Metrics:
Cited by: 14 works
Citation information provided by
Web of Science

Figures / Tables:

Fig. 1 Fig. 1: Structures of ligand 1 (left) and EuII1 (right).

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    Works referencing / citing this record:

    Samarium Diiodide Mediated Reactions in Total Synthesis
    journal, September 2009

    • Nicolaou, K. C.; Ellery, Shelby P.; Chen, Jason S.
    • Angewandte Chemie International Edition, Vol. 48, Issue 39
    • DOI: 10.1002/anie.200902151

    Visible-Light-Induced Photoredox Catalysis with a Tetracerium-Containing Silicotungstate
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    • Suzuki, Kosuke; Tang, Fei; Kikukawa, Yuji
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    A Chiral Metal Photocatalyst Architecture for Highly Enantioselective Photoreactions
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    • Amador, Adrian G.; Yoon, Tehshik P.
    • Angewandte Chemie International Edition, Vol. 55, Issue 7
    • DOI: 10.1002/anie.201511443

    A Molybdenum(0) Isocyanide Analogue of Ru(2,2′-Bipyridine) 3 2+ : A Strong Reductant for Photoredox Catalysis
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    • Büldt, Laura A.; Guo, Xingwei; Prescimone, Alessandro
    • Angewandte Chemie International Edition, Vol. 55, Issue 37
    • DOI: 10.1002/anie.201605571

    Photocatalytic C−C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex
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    • Guo, Jing-Jing; Hu, Anhua; Chen, Yilin
    • Angewandte Chemie International Edition, Vol. 55, Issue 49
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    • Prasad, Edamana; Knettle, Brian W.; Flowers, Robert A.
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    • Lenora, Chamika U.; Carniato, Fabio; Shen, Yimin
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    • DOI: 10.1002/chem.201702158

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    journal, April 2015


    Spectroscopic Characterization of the 3+ and 2+ Oxidation States of Europium in a Macrocyclic Tetraglycinate Complex
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    journal, August 2016


    Investigation into the Effects of a Trigonal-Planar Ligand Field on the Electronic Properties of Lanthanide(II) Tris(silylamide) Complexes (Ln = Sm, Eu, Tm, Yb)
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    • Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C.
    • The Journal of Organic Chemistry, Vol. 81, Issue 16
    • DOI: 10.1021/acs.joc.6b01449

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    • Douglas, James J.; Sevrin, Martin J.; Stephenson, Corey R. J.
    • Organic Process Research & Development, Vol. 20, Issue 7
    • DOI: 10.1021/acs.oprd.6b00125

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    journal, July 2015


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    • Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C.
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    • DOI: 10.1021/cr300503r

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    • DOI: 10.1021/ic500790q

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    journal, February 2005

    • Harkins, Seth B.; Peters, Jonas C.
    • Journal of the American Chemical Society, Vol. 127, Issue 7
    • DOI: 10.1021/ja043092r

    Unexpected Coordination Chemistry of Bisphenanthroline Complexes within Hybrid Materials:  A Mild Way to Eu 2+ Containing Materials with Bright Yellow Luminescence
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    • Journal of the American Chemical Society, Vol. 129, Issue 42
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    Generation of Powerful Tungsten Reductants by Visible Light Excitation
    journal, July 2013

    • Sattler, Wesley; Ener, Maraia E.; Blakemore, James D.
    • Journal of the American Chemical Society, Vol. 135, Issue 29
    • DOI: 10.1021/ja4047119

    Facile Synthesis of Z -Alkenes via Uphill Catalysis
    journal, February 2014

    • Singh, Kamaljeet; Staig, Shannon J.; Weaver, Jimmie D.
    • Journal of the American Chemical Society, Vol. 136, Issue 14
    • DOI: 10.1021/ja5019749

    Bespoke Photoreductants: Tungsten Arylisocyanides
    journal, January 2015

    • Sattler, Wesley; Henling, Lawrence M.; Winkler, Jay R.
    • Journal of the American Chemical Society, Vol. 137, Issue 3
    • DOI: 10.1021/ja510973h

    Photoinduced Reduction and Carbonylation of Organic Chlorides with Samarium Diiodide
    journal, March 1997

    • Ogawa, Akiya; Sumino, Yukihito; Nanke, Taizoh
    • Journal of the American Chemical Society, Vol. 119, Issue 11
    • DOI: 10.1021/ja963117p

    Aqueous Eu II -Containing Complex with Bright Yellow Luminescence
    journal, April 2015

    • Kuda-Wedagedara, Akhila N. W.; Wang, Chengcheng; Martin, Philip D.
    • Journal of the American Chemical Society, Vol. 137, Issue 15
    • DOI: 10.1021/jacs.5b02506

    Luminescent Ce(III) Complexes as Stoichiometric and Catalytic Photoreductants for Halogen Atom Abstraction Reactions
    journal, July 2015

    • Yin, Haolin; Carroll, Patrick J.; Anna, Jessica M.
    • Journal of the American Chemical Society, Vol. 137, Issue 29
    • DOI: 10.1021/jacs.5b05411

    Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling
    journal, August 2015

    • Nawrat, Christopher C.; Jamison, Christopher R.; Slutskyy, Yuriy
    • Journal of the American Chemical Society, Vol. 137, Issue 35
    • DOI: 10.1021/jacs.5b07678

    Cerium Photosensitizers: Structure–Function Relationships and Applications in Photocatalytic Aryl Coupling Reactions
    journal, May 2016

    • Yin, Haolin; Carroll, Patrick J.; Manor, Brian C.
    • Journal of the American Chemical Society, Vol. 138, Issue 18
    • DOI: 10.1021/jacs.6b02248

    Catalytic, Enantioselective Addition of Alkyl Radicals to Alkenes via Visible-Light-Activated Photoredox Catalysis with a Chiral Rhodium Complex
    journal, May 2016

    • Huo, Haohua; Harms, Klaus; Meggers, Eric
    • Journal of the American Chemical Society, Vol. 138, Issue 22
    • DOI: 10.1021/jacs.6b03399

    The Hexachlorocerate(III) Anion: A Potent, Benchtop Stable, and Readily Available Ultraviolet A Photosensitizer for Aryl Chlorides
    journal, December 2016

    • Yin, Haolin; Jin, Yi; Hertzog, Jerald E.
    • Journal of the American Chemical Society, Vol. 138, Issue 50
    • DOI: 10.1021/jacs.6b05712

    Synthesis and characterization of two nitrogen-donor cryptands
    journal, December 1993

    • Smith, Paul H.; Barr, Mary E.; Brainard, James R.
    • The Journal of Organic Chemistry, Vol. 58, Issue 27
    • DOI: 10.1021/jo00079a051

    Shining Light on Photoredox Catalysis: Theory and Synthetic Applications
    journal, January 2012

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    Photophysical characterization of a highly luminescent divalent-europium-containing azacryptate
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    Synthesis of uranium-in-cryptand complexes
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    Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
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    Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II)
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      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.