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König, B.: 2019 Science of Synthesis, 2018/6: Photocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-229-00162
Photocatalysis in Organic Synthesis

9 Gold in Photocatalysis

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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.; 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

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Abstract

Dual catalytic systems combining gold and photocatalysis are capable of facilitating redox-neutral coupling reactions that are otherwise seldom observed using gold catalysts alone. The challenging oxidation of gold(I) to gold(III) in these processes is achieved through two single-electron-transfer steps involving photogenerated organic radicals derived most commonly from arenediazonium salts. In addition to analogues of some classical cross-coupling processes that are tolerant of halogen functionalities, arylative 1,2-difunctionalization reactions of π-systems, combining the traditional π-Lewis acidity of gold catalysts with coupling, are accessible. These processes can be performed on alkene, allene, and alkyne substrates with the unique mechanistic features of dual gold/photoredox catalysis allowing for improved selectivity for cross coupling compared to that observed in alternative oxidative gold-catalyzed coupling methodologies.

Key words

photocatalysis - gold catalysis - photoredox catalysis - cross coupling - 1,2-difunctionalization - arylation - diazonium salts - dual catalysis - visible light - alkenes - allenes - alkynes - redox-neutral coupling - radical intermediates - aryl radicals
 
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