3.5.13 Silver-Promoted Coupling Reactions

J.-M. Weibel; A. Blanc; P. Pale

doi:10.1055/sos-SD-103-00201

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Brøndsted Nielsen, M. et al.: 2018 Science of Synthesis, 2018/1: Knowledge Updates 2018/1 DOI: 10.1055/sos-SD-103-00201

Knowledge Updates 2018/1

3.5.13 Silver-Promoted Coupling Reactions

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Editors: Brøndsted Nielsen, M.; Krause, N.; Rademann, J.; Ramsden, C. A.; Reissig, H.-U.

Authors: Ayad, T.; Bajić, M.; Blanc, A.; González-Bello, C.; Hashmi, A. S. K.; Hessel, V.; Kingston, M.; Pale, P.; Pirat, J.-L.; Pittelkow, M.; Ulfkjaer, A.; Virieux, D.; Volle, J.-N.; Weibel, J.-M.; Žnidaršič-Plazl, P.

Title: Knowledge Updates 2018/1

Print ISBN: 9783132423138; Online ISBN: 9783132423169; Book DOI: 10.1055/b-005-145253

1st edition © 2018 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

Science of Synthesis Knowledge Updates

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

Silver salts or complexes promote a variety of useful C—C bond-forming transformations in organic synthesis, usually under very mild conditions. In these reactions, silver can be engaged either as catalyst or cocatalyst, or as an organometallic reagent. Organosilver species act as mild nucleophiles toward alkyl halides or epoxides, but also toward carbonyl and imine derivatives and related heterocycles such as pyridines or quinolines. Silver can promote the homocoupling of a variety of organometallic reagents, of heterocycles, and of electron-deficient alkenes upon addition of the corresponding fluoride salts. Silver also promotes the cross coupling of alkyl or aryl halides, alkenes and alkynes, and even (het)arenes. Furthermore, silver salts often improve the efficiency of palladium-catalyzed cross-coupling reactions, or coupling reactions involving C—H activation or decarboxylation.

Key words

silver - C—C bond formation - homocoupling - cross coupling - catalysis

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