Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Kirsty L. Wilson, Alan R. Kennedy, Jane Murray, Ben Greatrex, Craig Jamieson and Allan J. B. Watson
Beilstein J. Org. Chem. 2016, 12, 2005–2011. https://doi.org/10.3762/bjoc.12.187

Supporting Information

Supporting Information File 1: Experimental procedures, analytical data, copies of NMR spectra, and single X-ray crystal diffraction data of 4b.
Format: PDF Size: 9.4 MB Download

Cite the Following Article

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation
Kirsty L. Wilson, Alan R. Kennedy, Jane Murray, Ben Greatrex, Craig Jamieson and Allan J. B. Watson
Beilstein J. Org. Chem. 2016, 12, 2005–2011. https://doi.org/10.3762/bjoc.12.187

How to Cite

Wilson, K. L.; Kennedy, A. R.; Murray, J.; Greatrex, B.; Jamieson, C.; Watson, A. J. B. Beilstein J. Org. Chem. 2016, 12, 2005–2011. doi:10.3762/bjoc.12.187

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 144.9 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Zeng, F.; Yu, B. doi:10.1002/9783527841943.ch8
  • Citarella, A.; Cavinato, M.; Amenta, A.; Nardini, M.; Silvani, A.; Passarella, D.; Fasano, V. A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene. European Journal of Organic Chemistry 2024. doi:10.1002/ejoc.202301305
  • Podversnik, H.; Camp, J. E.; Greatrex, B. W. Practical and scalable enantioselective synthesis of (+)-majoranolide from Cyrene. Organic & biomolecular chemistry 2024, 22, 950–953. doi:10.1039/d3ob01919e
  • Jeřábek, V.; Štejfa, V.; Klajmon, M.; Řehák, K. Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons. Journal of Chemical & Engineering Data 2023, 68, 3361–3376. doi:10.1021/acs.jced.3c00461
  • Ramos-Villaseñor, J. M.; Sotelo-Gil, J.; Rodil, S. E.; Frontana-Uribe, B. A. Dihydrolevoglucosenone (Cyrene™), a new possibility of an environmentally compatible solvent in synthetic organic electrochemistry. Faraday discussions 2023, 247, 182–194. doi:10.1039/d3fd00064h
  • Murata, Y.; Nishi, Y.; Matsumura, M.; Yasuike, S. Palladium-Catalyzed Cross-Coupling Reaction of Bis(cyclopentadienyl)diaryltitaniums with Terminal Alkynes. Reactions 2023, 4, 657–666. doi:10.3390/reactions4040037
  • Schulz, L.; Sawall, M.; Kockmann, N.; Röder, T. Chemometric tools for kinetic investigations of a homogeneously catalysed Sonogashira cross-coupling reaction in flow. Reaction Chemistry & Engineering 2023, 8, 2435–2445. doi:10.1039/d3re00173c
  • Webb, D. A.; Alsudani, Z.; Xu, G.; Gao, P.; Arnold, L. A. Improved 2-pyridyl reductive homocoupling reaction using biorenewable solvent Cyrene™ (dihydrolevoglucosenone). RSC sustainability 2023, 1, 1522–1529. doi:10.1039/d3su00005b
  • Islam, K.; Bhunia, B. K.; Mandal, G.; Nag, B.; Jaiswal, C.; Mandal, B. B.; Kumar, A. Room-Temperature, Copper-Free, and Amine-Free Sonogashira Reaction in a Green Solvent: Synthesis of Tetraalkynylated Anthracenes and In Vitro Assessment of Their Cytotoxic Potentials. ACS omega 2023, 8, 16907–16926. doi:10.1021/acsomega.3c00732
  • Melchiorre, M.; Budzelaar, P. H. M.; Cucciolito, M. E.; Esposito, R.; Santagata, E.; Ruffo, F. 1,3-Dioxolane compounds (DOXs) as biobased reaction media. Green Chemistry 2023, 25, 2790–2799. doi:10.1039/d3gc00227f
  • Sangon, S.; Supanchaiyamat, N.; Sherwood, J.; Macquarrie, D. J.; Noppawan, P.; Hunt, A. J. Application of hindered ether solvents for palladium catalyzed Suzuki-Miyaura, Sonogashira and cascade Sonogashira cross-coupling reactions. Organic & biomolecular chemistry 2023, 21, 2603–2609. doi:10.1039/d3ob00118k
  • Martinho, L. A.; Rosalba, T. P. F.; Sousa, G. G.; Gatto, C. C.; Politi, J. R. S.; Andrade, C. K. Z. Cyrene: a very reactive bio-based chiral ketone in diastereoselective Passerini reactions. Molecular diversity 2023, 28, 111–123. doi:10.1007/s11030-023-10618-6
  • Dekker, T.; Harteveld, J. W.; Wágner, G.; de Vries, M. C. M.; Custers, H.; van de Stolpe, A. C.; de Esch, I. J. P.; Wijtmans, M. Green Drug Discovery: Novel Fragment Space from the Biomass-Derived Molecule Dihydrolevoglucosenone (CyreneTM). Molecules (Basel, Switzerland) 2023, 28, 1777. doi:10.3390/molecules28041777
  • Stini, N. A.; Gkizis, P. L.; Kokotos, C. G. Cyrene: a bio-based solvent for the Mizoroki-Heck reaction of aryl iodides. Organic & biomolecular chemistry 2023, 21, 351–358. doi:10.1039/d2ob02012b
  • Huang, L.; Liu, Y.; Wan, J. Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction. Chinese Journal of Organic Chemistry 2023, 43, 2096. doi:10.6023/cjoc202212002
  • Citarella, A.; Amenta, A.; Passarella, D.; Micale, N. Cyrene: A Green Solvent for the Synthesis of Bioactive Molecules and Functional Biomaterials. International journal of molecular sciences 2022, 23, 15960. doi:10.3390/ijms232415960
  • Aich, D.; Kumar, P.; Ghorai, D.; Kanti Das, K.; Panda, S. Recent advances in the synthesis and reactivity of MIDA boronates. Chemical communications (Cambridge, England) 2022, 58, 13298–13316. doi:10.1039/d2cc04893k
  • do Carmo Pinheiro, R.; Welter, L. E.; Iglesias, B. A.; Back, D. F.; Marques, L. S.; Wayne Nogueira, C.; Zeni, G. Base‐Catalyzed Sequential 5‐exo‐dig/7‐endo‐dig Cyclization of (2‐Alkynylphenyl) Benzyl Ethers: Scope, Mechanism Studies, and Photophysical Properties. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200984
  • Hayes, G.; Laurel, M.; MacKinnon, D.; Zhao, T.; Houck, H. A.; Becer, C. R. Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers. Chemical reviews 2022, 123, 2609–2734. doi:10.1021/acs.chemrev.2c00354
  • Sullivan, C.; Zhang, Y.; Xu, G.; Christianson, L.; Luengo, F.; Halkoski, T.; Gao, P. Cyrene™ blends: a greener solvent system for organic syntheses. Green Chemistry 2022, 24, 7184–7193. doi:10.1039/d2gc01911f
Other Beilstein-Institut Open Science Activities