4 Cross-Dehydrogenative Coupling Involving Alkynes for C(sp2)—C(sp) Bond Formation
Buch
Herausgeber: Maiti, D.
Titel: Cross-Dehydrogenative Coupling
Print ISBN: 9783132455245; Online ISBN: 9783132455269; Buch-DOI: 10.1055/b000000640
1st edition © 2023. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Reference Libraries
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: 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.
Typ: Mehrbändiges Werk
Abstract
Cross-dehydrogenative coupling reactions represent one of the most environmentally friendly and atom-economic strategies to achieve carbon–carbon or carbon–heteroatom bond formation from non-prefunctionalized substrates, formally producing only dihydrogen as waste. Using terminal alkynes as one of the coupling partners in cross-dehydrogenative couplings, the sustainable synthesis of a myriad of alkynylated compounds is possible. In this review, the major advances in cross-dehydrogenative couplings involving alkynes are covered, with a focus on the formation of C(sp2)—C(sp) bonds, leading to alkynylated arenes, 1,3-enynes, and ynone derivatives. Synthetic strategies, reaction conditions, and the scope of each method are critically discussed, from early developments to date.
Schlüsselwörter
cross-dehydrogenative coupling - transition-metal catalysis - alkynes - cross coupling - alkynylation - C—H activation - radical chemistry - C—C bond formation - heterocycles - carbonyl compounds - aromatic compounds - 1,3-enynes- 1 Acetylene Chemistry: Chemistry, Biology, and Material Science. Diederich F, Stang PJ, Tykwinski RR. Wiley-VCH; Weinheim 2004
- 3 Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations. Trost BM, Li C.-J. Wiley-VCH; Weinheim 2014
-
24 Chen C.-H, Chai Y, Zhou Z.-X, Rao W.-H, Liu B, Liu L, Xu R, Liu Y.-J, Zeng M.-H. Org. Chem. Front. 2019; 6: 442
-
25 Bellina F, Biagetti M, Guariento S, Lessi M, Fausti M, Ronchi P, Rosadoni E. RSC Adv. 2021; 11: 25504
-
41 Leyva-Pérez A, Oliver-Meseguer J, Cabrero-Antonino JR, Rubio-Marqués P, Serna P, Al-Resayes SI, Corma A. ACS Catal. 2013; 3: 1865
-
43 Zhang L.-B, Hao X.-Q, Liu Z.-J, Zheng X.-X, Zhang S.-K, Niu J.-L, Song M.-P. Angew. Chem. Int. Ed. 2015; 54: 10012