2.4 Redox-Active Ligands in Catalysis for Single-Electron-Transfer Processes
Book
Editors: Fensterbank, L.; Ollivier, C.
Title: Free Radicals: Fundamentals and Applications in Organic Synthesis 2
Print ISBN: 9783132435544; Online ISBN: 9783132435551; Book DOI: 10.1055/b000000086
1st edition © 2021. 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 (Editor-in-Chief), A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Redox-active ligands are well known for their ability to stabilize electronic density on their scaffolds, and coordination complexes with such ligands are often stable, open-shell species. This property can be used as a means to favor single-electron transfer (SET) with external sources and devise catalytic radical manifolds. This chapter highlights selected representative reactions resulting in efficient and broad-scope catalytic methodologies. It covers nitrene and carbene radical reactivity, as well as radical trifluoromethylation.
Key words
redox-active ligands - radicals - single-electron transfer - nitrenes - carbenes - trifluoromethylation - aziridines - cyclopropanes - C—H functionalization - porphyrins - transition-metal complexes-
4 Goswami M, Lyaskovskyy V, Domingos SR, Buma WJ, Woutersen S, Troeppner O, Ivanović-Burmazović I, Lu H, Cui X, Zhang XP, Reijerse EJ, DeBeer S, van Schooneveld MM, Pfaff FF, Ray K, de Bruin B. J. Am. Chem. Soc. 2015; 137: 5468
-
24 Lyaskovskyy V, Olivos Suarez AI, Lu H, Jiang H, Zhang XP, de Bruin B. J. Am. Chem. Soc. 2011; 133: 12264
-
25 van Leest NP, Tepaske MA, Oudsen J.-PH, Venderbosch B, Rietdijk NR, Siegler MA, Tromp M, van der Vlugt JI, de Bruin B. J. Am. Chem. Soc. 2020; 142: 552
-
27 Kundu S, Miceli E, Farquhar E, Pfaff FF, Kuhlmann U, Hildebrandt P, Braun B, Greco C, Ray K. J. Am. Chem. Soc. 2012; 134: 14710
-
28 Maestre L, Sameera WMC, Mar Díaz-Requejo M, Maseras F, Pérez PJ. J. Am. Chem. Soc. 2013; 135: 1338
-
29 Ren Y, Cheaib K, Jacquet J, Vezin H, Fensterbank L, Orio M, Blanchard S, Desage-El Murr M. Chem.–Eur. J. 2018; 24: 5086
-
30 Ren Y, Forté J, Cheaib K, Vanthuyne N, Fensterbank L, Vezin H, Orio M, Blanchard S, Desage-El Murr M. iScience 2020; 23: 100955
-
31 Broere DLJ, de Bruin B, Reek JNH, Lutz M, Dechert S, van der Vlugt JI. J. Am. Chem. Soc. 2014; 136: 11574
-
33 Fujita D, Sugimoto H, Shiota Y, Morimoto Y, Yoshizawa K, Itoh S. Chem. Commun. (Cambridge) 2017; 53: 4849
-
36 Penoni A, Wanke R, Tollari S, Gallo E, Musella D, Ragaini F, Demartin F, Cenini S. Eur. J. Inorg. Chem. 2003; 1452
-
45 Robertson JFR, Come SE, Jones SE, Beex L, Kaufmann M, Makris A, Nortier JWR, Possinger K, Rutqvist L.-E. Eur. J. Cancer 2005; 41: 346