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Cazin, C.  et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00044
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.2.1 Suzuki–Miyaura Coupling

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Editors: Cazin, C. ; Nolan, S.

Authors: Albrecht, M.; Baudrenghien, L.; Bielawski, C.; Biffis, A.; Cavallo, L.; Cazin, C. ; César, V.; Chetcuti, M.; Cuenca, A.; de Frémont, P.; Elie, M.; Fairlamb, I.; Falivene, L.; Fernandez Gutierrez, M. E.; Gagné, M. R.; Gaillard, S.; Huynh, H.; Kalck, P.; Kuwano, R.; Lastovickova, D.; Lavigne, G.; Makida, Y.; Marko, I.; Martin, A.; Nahra, F. ; Nakao, Y.; Ogasawara, M. ; Payne, P.; Renaud, J.; Ronson, T.; Ruamps, M.; Segarra Almela, C.; Teator, A.; Trzeciak, A.; Tubaro, C.; Urrutigoity, M.; Vummaleti, S.; Whittlesey, M.; Yuan, D.

Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1

Print ISBN: 9783132012813; Online ISBN: 9783132407633; Book DOI: 10.1055/b-004-132254

1st edition © 2017. 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: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

The Suzuki–Miyaura reaction of an organoboronic acid (usually an arylboronic acid) with an organo halide (typically an aryl halide) to generate a new C—C bond is one of the most valuable methods for C–C bond formation. Since the ascension of N-heterocyclic carbenes (NHCs) to occupy the position of key ligands in the repertoire of synthetic organometallic chemists, metal complexes based on these ligands have become important as catalysts for the Suzuki–Miyaura reaction. Most metal–NHC complexes used for Suzuki–Miyaura coupling are based on palladium, but an increasingly important contribution is being played by nickel-based complexes. This chapter reviews the state of the art of Suzuki–Miyaura coupling reactions catalyzed by metal–NHC complexes, with a focus on systems with broad applicability, and especially those that can be applied to “difficult” reactions such as the coupling of aryl chlorides or sterically hindered substrates. The relatively undeveloped fields of asymmetric Suzuki–Miyaura reactions and Suzuki–Miyaura reactions in water, both catalyzed by metal–NHC complexes, are also covered.

Key words

Suzuki–Miyaura coupling - N-heterocyclic carbenes - palladium catalysis - nickel catalysis - biaryls - aryl halides - boronic acids - asymmetric synthesis - aqueous media
 
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