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König, B.: 2019 Science of Synthesis, 2018/6: Photocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-229-00087
Photocatalysis in Organic Synthesis

4 Photocatalytic Oxidative C–C Bond Formation

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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. ; Molander, G. A. ; Mudd, R. J.; Ollivier, C.; Pandey, G.; Phelan, J.; 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 (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

Also available at
 

Abstract

This chapter summarizes some important examples of carbon–carbon bond-forming reactions at the α-position of tertiary amines using photoredox catalysis. The photocatalytic single-electron oxidation of tertiary amines leads to the generation of an amine radical cation, from which two highly reactive and synthetically useful intermediates, iminium ions and α-aminoalkyl radicals, can be produced. Iminium ion intermediates, being electrophilic in nature, react with a range of carbon nucleophiles forming new carbon–carbon bonds. On the other hand, the α-aminoalkyl radical, an electron-rich radical, adds efficiently to electron-deficient unsaturated systems resulting in carbon–carbon bond-forming reactions. This chapter also highlights some examples of carbon–carbon bond-forming reaction by nucleophilic/radical addition to photocatalytically generated arene radical cations.

Key words

Keywords: - photocatalysis - photoredox catalysis - carbon–carbon bond formation - tertiary amines - iminium ions - α-aminoalkyl radicals - arene radical cations - cross coupling - aza-Henry reaction - Mannich reaction - Friedel–Crafts reaction - Strecker reaction - Sakurai reaction - radical addition - Michael addition - radical–radical coupling - heteroarylation - arylation - carbocyclization - acylation - alkylation
 
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