The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups

Yi Wang, Ricardo Callejo, Alexandra M. Z. Slawin and David O’Hagan
Beilstein J. Org. Chem. 2014, 10, 18–25. https://doi.org/10.3762/bjoc.10.4

Supporting Information

Supporting Information File 1: Experimental part.
Format: PDF Size: 4.9 MB Download

Cite the Following Article

The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups
Yi Wang, Ricardo Callejo, Alexandra M. Z. Slawin and David O’Hagan
Beilstein J. Org. Chem. 2014, 10, 18–25. https://doi.org/10.3762/bjoc.10.4

How to Cite

Wang, Y.; Callejo, R.; Slawin, A. M. Z.; O’Hagan, D. Beilstein J. Org. Chem. 2014, 10, 18–25. doi:10.3762/bjoc.10.4

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.

Citations to This Article

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

Scholarly Works

  • Poole, W. G.; Peron, F.; Fox, S. J.; Wells, N.; Skylaris, C.-K.; Essex, J. W.; Kuprov, I.; Linclau, B. Conformational Analysis of 1,3-Difluorinated Alkanes. The Journal of organic chemistry 2024, 89, 8789–8803. doi:10.1021/acs.joc.4c00670
  • Cong, F.; Sun, G.-Q.; Ye, S.-H.; Hu, R.; Rao, W.; Koh, M. J. A Bimolecular Homolytic Substitution-Enabled Platform for Multicomponent Cross-Coupling of Unactivated Alkenes. Journal of the American Chemical Society 2024, 146, 10274–10280. doi:10.1021/jacs.4c02284
  • Epplin, R. C.; Gulder, T. Enyne difluorination. Nature chemistry 2023, 15, 1484–1485. doi:10.1038/s41557-023-01352-5
  • Zhang, Z.-Q.; Wang, C.-Q.; Li, L.-J.; Piper, J. L.; Peng, Z.-H.; Ma, J.-A.; Zhang, F.-G.; Wu, J. Programmable synthesis of difluorinated hydrocarbons from alkenes through a photocatalytic linchpin strategy. Chemical science 2023, 14, 11546–11553. doi:10.1039/d3sc03951j
  • Wang, Z.-X.; Livingstone, K.; Hümpel, C.; Daniliuc, C. G.; Mück-Lichtenfeld, C.; Gilmour, R. Regioselective, catalytic 1,1-difluorination of enynes. Nature chemistry 2023, 15, 1515–1522. doi:10.1038/s41557-023-01344-5
  • Gauthier, R.; Paquin, J.-F. Hydrofluorination of Alkynes: From (E) to (Z). Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202301896. doi:10.1002/chem.202301896
  • Yue, W.-J.; Martin, R. α-Difluoroalkylation of Benzyl Amines with Trifluoromethylarenes. Angewandte Chemie (International ed. in English) 2023, 62, e202310304. doi:10.1002/anie.202310304
  • Yue, W.; Martin, R. α‐Difluoroalkylation of Benzyl Amines with Trifluoromethylarenes. Angewandte Chemie 2023, 135. doi:10.1002/ange.202310304
  • Chen, S.; Zou, S.; Xi, C. Photocatalyzed 2∶2 Coupling of Styrene and BrCF2CO2Me: A Facile Synthesis of Bis-difluoroacetylated Hexestrol Derivatives. Chinese Journal of Organic Chemistry 2023, 43, 1157. doi:10.6023/cjoc202210009
  • Arnold, M. R.; Langelier, M.-F.; Gartrell, J.; Kirby, I. T.; Sanderson, D. J.; Bejan, D. S.; Šileikytė, J.; Sundalam, S. K.; Nagarajan, S.; Marimuthu, P.; Duell, A. K.; Shelat, A. A.; Pascal, J. M.; Cohen, M. S. Allosteric regulation of DNA binding and target residence time drive the cytotoxicity of phthalazinone-based PARP-1 inhibitors. Cell chemical biology 2022, 29, 1694–1708.e10. doi:10.1016/j.chembiol.2022.11.006
  • Feng, X.-T.; Ren, J.-X.; Gao, X.; Min, Q.-Q.; Zhang, X. 3,3-Difluoroallyl Sulfonium Salts: Practical and Bench-Stable Reagents for Highly Regioselective gem-Difluoroallylations. Angewandte Chemie (International ed. in English) 2022, 61, e202210103. doi:10.1002/anie.202210103
  • Feng, X.; Ren, J.; Gao, X.; Min, Q.; Zhang, X. 3,3‐Difluoroallyl Sulfonium Salts: Practical and Bench‐Stable Reagents for Highly Regioselective gem‐Difluoroallylations. Angewandte Chemie 2022, 134. doi:10.1002/ange.202210103
  • Yue, W.-J.; Day, C. S.; Brenes Rucinski, A. J.; Martin, R. Catalytic Hydrodifluoroalkylation of Unactivated Olefins. Organic letters 2022, 24, 5109–5114. doi:10.1021/acs.orglett.2c01941
  • Ren, X.; Gao, X.; Min, Q.-Q.; Zhang, S.; Zhang, X. (Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes. Chemical science 2022, 13, 3454–3460. doi:10.1039/d1sc07061d
  • Zhi-Qiang, L.; Cheng-Qiang, W.; Chao, F. Facile Synthesis of Allylic gem-Difluorides Enabled by Novel 3,3-Difluoroallyl Sulfonium Salts. Chinese Journal of Organic Chemistry 2022, 42, 3906. doi:10.6023/cjoc202200065
  • Xi, C.; Chen, S.; Zou, S.; Chen, C. Photoredox-Catalyzed 2:2 Coupling of Aryl Ethylene and Brcf2co2me: A Facile Synthesis of Two Difluoroacetylated Hexestrol Derivatives. SSRN Electronic Journal 2022. doi:10.2139/ssrn.4193557
  • Shaitanova, E. N.; Balabon, O. A.; Rybakova, A. N.; Khlebnicova, T. S.; Lakhvich, F. A.; Gerus, I. I. Synthesis of functionalized fluoroalkyl pyrimidines and pyrazoles from fluoroalkyl enones. Journal of Fluorine Chemistry 2021, 252, 109905. doi:10.1016/j.jfluchem.2021.109905
  • Chang, H.-J.; Lee, J.-H. Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties. Molecules (Basel, Switzerland) 2021, 26, 4015. doi:10.3390/molecules26134015
  • Akiyama, S.; Oyama, N.; Endo, T.; Kubota, K.; Ito, H. A Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins. Journal of the American Chemical Society 2021, 143, 5260–5268. doi:10.1021/jacs.1c02050
  • Troup, R. I.; Jeffries, B.; Saudain, R. E.-B.; Georgiou, E.; Fish, J.; Scott, J. S.; Chiarparin, E.; Fallan, C.; Linclau, B. Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs. The Journal of organic chemistry 2021, 86, 1882–1900. doi:10.1021/acs.joc.0c02810
Other Beilstein-Institut Open Science Activities