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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-223-00051
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.2.2 Cross-Coupling Reactions Other Than 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

Cross coupling between a main-group organometallic nucleophile and an organic electrophile is one of the most powerful C—C bond-forming reactions in modern organic synthesis. Various palladium–N-heterocyclic carbene (NHC) complexes have been utilized in a wide range of cross-coupling reactions. The palladium–NHC systems outperform the classical palladium–phosphine catalysts in many cases, and they have solved several long-standing limitations of the classical cross-coupling protocols. This chapter covers cross couplings mediated by palladium–NHC complexes in which the nucleophile is an organomagnesium (Kumada–Tamao–Corriu coupling), an organozinc (Negishi coupling), an organotin (Stille coupling), an organosilicon (Hiyama coupling), or an organolithium, as well as Sonogashira-type couplings of alkynes.

Key words

cross coupling - N-heterocyclic carbenes - palladium catalysis - organomagnesium - Kumada–Tamao–Corriu coupling - organozinc - Negishi coupling - organotin - Stille coupling - organosilicon - Hiyama coupling - organolithium - Sonogashira coupling
 
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