20.2. 1.9 Synthesis of Alkanoic Acids Using Carbon Dioxide through Catalytic C—C Bond-Forming Reactions
Buch
Herausgeber: Campagne, J.-M. ; Donohoe, T. J.; Drabowicz, J. ; Fuerstner, A. ; Jiang, X. ; Wang, M. ; Wirth, T.
Titel: Knowledge Updates 2024/3
Online ISBN: 9783132457089; Buch-DOI: 10.1055/b000000969
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Knowledge Updates
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
In recent years, there has been growing interest in utilizing carbon dioxide as a feedstock for organic synthesis due to its abundance, low cost, and environmentally benign nature, with a particular focus on the catalytic synthesis of alkanoic acids from readily available starting materials via C–C bond formation. This review provides a comprehensive overview of this approach, covering the synthesis of alkanoic acids from alkyl (pseudo)halides, alkyl alcohol derivatives, isolable organometallic species, alkenes, and alkanes via C(sp3)–H bond activation. The versatility and practicality demonstrated for these methods underscores the significance of this approach in accessing valuable carboxylic acid derivatives from carbon dioxide.
Schlüsselwörter
carbon dioxide - carboxylation - carboxylic acids - C–C bond formation - transition metals - visible light - photoredox - electrolysis - nickel - palladium - reductants- 10 Wang L, Li T, Perveen S, Zhang S, Wang X, Ouyang Y, Li P. Angew. Chem. Int. Ed. 2022; 61: e202213943
- 15 Sahoo B, Bellotti P, Juliá-Hernández F, Meng Q.-Y, Crespi S, König B, Martin R. Chem.–Eur. J. 2019; 25: 9001
- 16 Sun G.-Q, Zhang W, Liao L.-L, Li L, Nie Z.-H, Wu J.-G, Zhang Z, Yu D.-G. Nat. Commun. 2021; 12: 7086
- 19 Jiao K.-J, Li Z.-M, Xu X.-T, Zhang L.-P, Li Y.-Q, Zhang K, Mei T.-S. Org. Chem. Front. 2018; 5: 2244
- 22 van Gemmeren M, Börjesson M, Tortajada A, Sun S.-Z, Okura K, Martin R. Angew. Chem. Int. Ed. 2017; 56: 6558
- 25 Ran C.-K, Niu Y.-N, Song L, Wei M.-K, Cao Y.-F, Luo S.-P, Yu Y.-M, Liao L.-L, Yu D.-G. ACS Catal. 2022; 12: 18
- 39 Ostapowicz TG, Schmitz M, Krystof M, Klankermayer J, Leitner W. Angew. Chem. Int. Ed. 2013; 52: 12 119
- 45 Butcher TW, McClain EJ, Hamilton TG, Perrone TM, Kroner KM, Donohoe GC, Akhmedov NG, Petersen JL, Popp BV. Org. Lett. 2016; 18: 6428
- 46 Juhl M, Laursen SLR, Huang Y, Nielsen DU, Daasbjerg K, Skrydstrup T. ACS Catal. 2017; 7: 1392 corrigendum: ACS Catal. 2017; 7: 2247