Download PDF
König, B.: 2019 Science of Synthesis, 2018/6: Photocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-229-00149
Photocatalysis in Organic Synthesis

8 Copper-Based Photocatalysts for Visible-Light-Mediated Organic Transformations

More Information

Book

Editor: König, B.

Authors: Akita, M.; Albero, J.; Amador, A. G.; Ashley, M. A.; Brasholz, M.; Corcé, V.; DiRocco, D. A.; Dix, S.; Ehrnsberger, P.; Fensterbank, L.; Gaida, F.; García, H.; Ghosh, I.; Gilmour, R.; Griesbeck, A. G.; Gutiérrez Bonet, Á.; Hepburn, H. B.; Hopkinson, M. N.; Kelly, C. B.; Koike, T.; Laha, R.; Lang, S. B.; Leonori, D.; Lévêque, C.; Li, P.; Lu, L.-Q.; Matsui, J. K.; Melchiorre, P.; Metternich, J. B.; Molander, G. A.; Mudd, R. J.; Ollivier, C.; Pandey, G.; Phelan, J. P.; Reiser, O.; Rey, Y. P.; Rovis, T.; Ruffoni, A.; Scholz, S. O.; Schultz, D. M.; Skubi, K. L.; Speckmeier, E.; Thullen, S. M.; Vollmer, M.; Wang, L.; Wang, M.; Wei, Y.; Xiao, W.-J.; Yoon, T. P.; Zeitler, K.; Zhou, Q.-Q.

Title: Photocatalysis in Organic Synthesis

Print ISBN: 9783132417021; Online ISBN: 9783132417069; Book DOI: 10.1055/b-006-161273

1st edition © 2019. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

Copper(I) and copper(II) complexes prove to be a powerful alternative to common photocatalysts based on ruthenium, iridium, or organic dyes. A distinct feature is their ability to interact with substrates beyond electron or energy transfer, allowing unique transformations that are otherwise not possible.

Key words

photocatalysis - asymmetric synthesis - aziridines - cycloadditions - cyclobutanes - cyclopropanes - Diels–Alder - endoperoxides - Lewis acids - nitrenes - photochemistry - radical anion - radical cation - triplet state - visible light - [2 + 1] - [2 + 2] - [3 + 2] - [4 + 2] - [2 + 2 + 2]
 
  • 1 Ahn B.-T, McMillin DR. Inorg. Chem. 1978; 17: 2253
  • 2 McMillin DR, Buckner MT, Ahn BT. Inorg. Chem. 1977; 16: 943
  • 3 Schwendiman DP, Kutal C. J. Am. Chem. Soc. 1977; 99: 5677
  • 4 Grutsch PA, Kutal C. J. Am. Chem. Soc. 1979; 101: 4228
  • 5 Mitani M, Nakayama M, Koyama K. Tetrahedron Lett. 1980; 21: 4457
  • 6 Mitani M, Kato I, Koyama K. J. Am. Chem. Soc. 1983; 105: 6719
  • 7 Balili MNC, Pintauer T. Dalton Trans. 2011; 40: 3060
    PubMed
  • 8 Kern J.-M, Sauvage J.-P. J. Chem. Soc., Chem. Commun. 1987; 546
  • 9 Hernandez-Perez AC, Vlassova A, Collins SK. Org. Lett. 2012; 14: 2988
    PubMed
  • 10 Sagadevan A, Hwang KC. Adv. Synth. Catal. 2012; 354: 3421
  • 11 Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem.–Eur. J. 2012; 18: 7336
    PubMed
  • 12 Paria S, Reiser O. ChemCatChem 2014; 6: 2477
  • 13 Reiser O. Acc. Chem. Res. 2016; 49: 1990
    PubMed
  • 14 McLean EB, Lee A.-L. Tetrahedron 2018; 74: 4881
  • 15 Minozzi C, Caron A, Grenier-Petel J.-C, Santandrea J, Collins SK. Angew. Chem. Int. Ed. 2018; 57: 5477
    PubMed
  • 16 Hernandez-Perez AC, Collins SK. Angew. Chem. Int. Ed. 2013; 52: 12696
    PubMed
  • 17 Collins SK unpublished results; personal communication
  • 18 Sagadevan A, Lyu P.-C, Hwang KC. Green Chem. 2016; 18: 4526
  • 19 Sagadevan A, Charpe VP, Ragupathi A, Hwang KC. J. Am. Chem. Soc. 2017; 139: 2896
    PubMed
  • 20 Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CRJ. J. Am. Chem. Soc. 2011; 133: 4160
    PubMed
  • 21 Paria S, Pirtsch M, Kais V, Reiser O. Synthesis 2013; 45: 2689
  • 22 Bagal DB, Kachkovskyi G, Knorn M, Rawner T, Bhanage BM, Reiser O. Angew. Chem. Int. Ed. 2015; 54: 6999
    PubMed
  • 23 Oh SH, Malpani YR, Ha N, Jung Y.-S, Han SB. Org. Lett. 2014; 16: 1310
    PubMed
  • 24 Tang X.-J, Dolbier Jr WR. Angew. Chem. Int. Ed. 2015; 54: 4246
    PubMed
  • 25 Rawner T, Knorn M, Lutsker E, Hossain A, Reiser O. J. Org. Chem. 2016; 81: 7139
    PubMed
  • 26 Rawner T, Lutsker E, Kaiser CA, Reiser O. ACS Catal. 2018; 8: 3950
    Crossref
  • 27 Liu Z, Chen H, Lv Y, Tan X, Shen H, Yu H.-Z, Li C. J. Am. Chem. Soc. 2018; 140: 6169
    PubMed
  • 28 Knorn M, Rawner T, Czerwieniec R, Reiser O. ACS Catal. 2015; 5: 5186
  • 29 Baralle A, Fensterbank L, Goddard J.-P, Ollivier C. Chem.–Eur. J. 2013; 19: 10809
    PubMed
  • 30 Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science (Washington, D. C.) 2016; 351: 681
    PubMed
  • 31 Matier CD, Schwaben J, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 17707
    PubMed
  • 32 Rabet PTG, Fumagalli G, Boyd S, Greaney MF. Org. Lett. 2016; 18: 1646
    PubMed
  • 33 Fumagalli G, Rabet PTG, Boyd S, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11481
    PubMed
  • 34 Hossain A, Vidyasagar A, Eichinger C, Lankes C, Phan J, Rehbein J, Reiser O. Angew. Chem. Int. Ed. 2018; 57: 8288
    PubMed