Crossref journal-article
Springer Science and Business Media LLC
Nature Communications (297)
Bibliography

Choi, S., Kim, Y. J., Kim, S. M., Yang, J. W., Kim, S. W., & Cho, E. J. (2014). Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator. Nature Communications, 5(1).

Authors 6
  1. Sungkyu Choi (first)
  2. Ye Ji Kim (additional)
  3. Sun Min Kim (additional)
  4. Jung Woon Yang (additional)
  5. Sung Wng Kim (additional)
  6. Eun Jin Cho (additional)
References 40 Referenced 113
  1. Müller, K., Faeh, C. & Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition. Science 317, 1881–1886 (2007). (10.1126/science.1131943) / Science by K Müller (2007)
  2. O’Hagan, D. Understanding organofluorine chemistry. An introduction to the C-F bond. Chem. Soc. Rev. 37, 308–319 (2008). (10.1039/B711844A) / Chem. Soc. Rev. by D O’Hagan (2008)
  3. Yamazaki, T., Taguchi, T. & Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology Wiley-Blackwell (2009).
  4. Gouverneur, V. & Müller, K. Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications Imperial College Press (2012). (10.1142/p746)
  5. Jeschke, P. The unique role of fluorine in the design of active ingredients for modern crop production. Chembiochem 5, 570–589 (2004). (10.1002/cbic.200300833) / Chembiochem by P Jeschke (2004)
  6. Tomashenko, O. A. & Grushin, V. V. Aromatic trifluoromethylation with metal complexes. Chem. Rev. 111, 4475–4521 (2011). (10.1021/cr1004293) / Chem. Rev. by OA Tomashenko (2011)
  7. Studer, A. A. ‘Renaissance’ in radical trifluoromethylation. Angew. Chem. Int. Ed. 51, 8950–8958 (2012). (10.1002/anie.201202624) / Angew. Chem. Int. Ed. by AA Studer (2012)
  8. Besset, T., Schneider, C. & Cahard, D. Tamed arene and heteroarene trifluoromethylation. Angew. Chem. Int. Ed. 51, 5048–5050 (2012). (10.1002/anie.201201012) / Angew. Chem. Int. Ed. by T Besset (2012)
  9. Liang, T., Neumann, C. N. & Ritter, T. Introduction of fluorine and fluorine-containing functional groups. Angew. Chem. Int. Ed. 52, 8214–8264 (2013). (10.1002/anie.201206566) / Angew. Chem. Int. Ed. by T Liang (2013)
  10. Oishi, M., Kondo, H. & Amii, H. Aromatic trifluoromethylation catalytic in copper. Chem. Commun. 14, 1909–1911 (2009). (10.1039/b823249k) / Chem. Commun. by M Oishi (2009)
  11. Xu, J. et al. Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent. Chem. Commun. 47, 4300–4302 (2011). (10.1039/c1cc10359h) / Chem. Commun. by J Xu (2011)
  12. Cho, E. J. et al. The palladium-catalyzed trifluoromethylation of aryl chlorides. Science 328, 1679–1681 (2010). (10.1126/science.1190524) / Science by EJ Cho (2010)
  13. Nagib, D. A. & MacMillan, D. W. C. Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis. Nature 480, 224–228 (2011). (10.1038/nature10647) / Nature by DA Nagib (2011)
  14. Morimoto, H., Tsubogo, T., Litvinas, N. D. & Hartwig, J. F. A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides. Angew. Chem. Int. Ed. 50, 3793–3798 (2011). (10.1002/anie.201100633) / Angew. Chem. Int. Ed. by H Morimoto (2011)
  15. Iqbal, N., Choi, S., Ko, E. & Cho, E. J. Trifluoromethylation of heterocycles via visible light photoredox catalysis. Tetrahedron Lett. 53, 2005–2008 (2012). (10.1016/j.tetlet.2012.02.032) / Tetrahedron Lett. by N Iqbal (2012)
  16. Ye, Y. & Sanford, M. S. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I. J. Am. Chem. Soc. 134, 9034–9037 (2012). (10.1021/ja301553c) / J. Am. Chem. Soc. by Y Ye (2012)
  17. Danoun, G., Bayarmagnai, B., Grünberg, M. F. & Gooßen, L. J. Sandmeyer trifluoromethylation of arenediazonium tetrafluoroborates. Angew. Chem. Int. Ed. 52, 7972–7975 (2013). (10.1002/anie.201304276) / Angew. Chem. Int. Ed. by G Danoun (2013)
  18. Straathof, N. J. W. et al. Rapid trifluoromethylation and perfluoroalkylation of five-membered heterocycles by photoredox catalysis in continuous flow. ChemSusChem 7, 1612–1617 (2014). (10.1002/cssc.201301282) / ChemSusChem by NJW Straathof (2014)
  19. Dye, J. L. Electrides: ionic salts with electrons as the anions. Science 247, 663–668 (1990). (10.1126/science.247.4943.663) / Science by JL Dye (1990)
  20. Kitano, M. et al. Ammonia synthesis using a stable electride as an electron donor and reversible hydrogen store. Nat. Chem. 4, 934–940 (2012). (10.1038/nchem.1476) / Nat. Chem. by M Kitano (2012)
  21. Toda, Y. et al. Work function of a room-temperature, stable electride [Ca24Al28O64]4+(e–)4 . Adv. Mater. 19, 3564–3569 (2007). (10.1002/adma.200700663) / Adv. Mater. by Y Toda (2007)
  22. Dye, J. L. Electrides: from 1D Heisenberg chains to 2D pseudo-metals. Inorg. Chem. 36, 3816–3826 (1997). (10.1021/ic970551z) / Inorg. Chem. by JL Dye (1997)
  23. Lee, K., Kim, S. W., Toda, Y., Matsuishi, S. & Hosono, H. Dicalcium nitride as a two-dimensional electride with an anionic electron layer. Nature 494, 336–340 (2013). (10.1038/nature11812) / Nature by K Lee (2013)
  24. Liu, T. & Shen, Q. Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent. Org. Lett. 13, 2342–2345 (2011). (10.1021/ol2005903) / Org. Lett. by T Liu (2011)
  25. Cho, E. J. & Buchwald, S. L. The palladium-catalyzed trifluoromethylation of vinyl sulfonates. Org. Lett. 13, 6552–6555 (2011). (10.1021/ol202885w) / Org. Lett. by EJ Cho (2011)
  26. Parsons, A. T., Senecal, T. D. & Buchwald, S. L. Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates. Angew. Chem. Int. Ed. 51, 2947–2950 (2012). (10.1002/anie.201108267) / Angew. Chem. Int. Ed. by AT Parsons (2012)
  27. He, Z., Luo, T., Hu, M., Cao, Y. & Hu, J. Copper-catalyzed Di- and trifluoromethylation of α,β-unsaturated carboxylic acids: a protocol for vinylic fluoroalkylations. Angew. Chem. Int. Ed. 51, 3944–3947 (2012). (10.1002/anie.201200140) / Angew. Chem. Int. Ed. by Z He (2012)
  28. Wallentin, C. J., Nguyen, J. D., Finkbeiner, P. & Stephenson, C. R. J. Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts. J. Am. Chem. Soc. 134, 8875–8884 (2012). (10.1021/ja300798k) / J. Am. Chem. Soc. by CJ Wallentin (2012)
  29. Yasu, Y., Koike, T. & Akita, M. Three-component oxytrifluoromethylation of alkenes: highly efficient and regioselective difunctionalization of C=C bonds mediated by photoredox catalysts. Angew. Chem. Int. Ed. 51, 9567–9571 (2012). (10.1002/anie.201205071) / Angew. Chem. Int. Ed. by Y Yasu (2012)
  30. Iqbal, N., Choi, S., Kim, E. & Cho, E. J. Trifluoromethylation of alkenes by visible light photoredox catalysis. J. Org. Chem. 77, 11383–11387 (2012). (10.1021/jo3022346) / J. Org. Chem. by N Iqbal (2012)
  31. Yasu, Y., Koike, T. & Akita, M. Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis. Chem. Commun. 49, 2037–2039 (2013). (10.1039/c3cc39235j) / Chem. Commun. by Y Yasu (2013)
  32. Kim, E., Choi, S., Kim, H. & Cho, E. J. Generation of CF3-containing epoxides and aziridines by visible-light-driven trifluoromethylation of allylic alcohols and amines. Chem. Eur. J. 19, 6209–6212 (2013). (10.1002/chem.201300564) / Chem. Eur. J. by E Kim (2013)
  33. Deb, A. et al. Oxidative trifluoromethylation of unactivated olefins: an efficient and practical synthesis of α-trifluoromethyl-substituted ketones. Angew. Chem. Int. Ed. 52, 9747–9750 (2013). (10.1002/anie.201303576) / Angew. Chem. Int. Ed. by A Deb (2013)
  34. Mizuta, S. et al. Catalytic hydrotrifluoromethylation of unactivated alkenes. J. Am. Chem. Soc. 135, 2505–2508 (2013). (10.1021/ja401022x) / J. Am. Chem. Soc. by S Mizuta (2013)
  35. Wilger, D. J., Gesmundo, N. J. & Nicewicz, D. A. Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system. Chem. Sci. 4, 3160–3165 (2013). (10.1039/c3sc51209f) / Chem. Sci. by DJ Wilger (2013)
  36. Wu, X., Chu, L. & Qing, F.-L. Silver-catalyzed hydrotrifluoromethylation of unactivated alkenes with CF3SiMe3 . Angew. Chem. Int. Ed. 52, 2198–2202 (2013). (10.1002/anie.201208971) / Angew. Chem. Int. Ed. by X Wu (2013)
  37. Iqbal, N., Jung, J., Park, S. & Cho, E. J. Controlled trifluoromethylaion reactions of alkynes through visible-light photoredox caltalysis. Angew. Chem. Int. Ed. 53, 539–542 (2014). (10.1002/anie.201308735) / Angew. Chem. Int. Ed. by N Iqbal (2014)
  38. Christophorou, L. G. & Olthoff, J. K. Electron interactions with CF3I. J. Phys. Chem. Ref. Data 29, 553–569 (2000). (10.1063/1.1318910) / J. Phys. Chem. Ref. Data by LG Christophorou (2000)
  39. Kim, H. & Lee, C. Visible-light-induced photocatalytic reductive transformations of organohalides. Angew. Chem. Int. Ed. 51, 12303–12306 (2012). (10.1002/anie.201203599) / Angew. Chem. Int. Ed. by H Kim (2012)
  40. Nguyen, J. D., DAmato, E. M., Narayanam, J. M. R. & Stephenson, C. R. J. Engaging unactivated alkyl, alkenyl and aryliodides in visible-light-mediated free radical reactions. Nat. Chem. 4, 854–859 (2012). (10.1038/nchem.1452) / Nat. Chem. by JD Nguyen (2012)
Dates
Type When
Created 10 years, 11 months ago (Sept. 12, 2014, 8:39 a.m.)
Deposited 2 years, 7 months ago (Jan. 5, 2023, 10 p.m.)
Indexed 1 month, 3 weeks ago (July 7, 2025, 5:07 a.m.)
Issued 10 years, 11 months ago (Sept. 12, 2014)
Published 10 years, 11 months ago (Sept. 12, 2014)
Published Online 10 years, 11 months ago (Sept. 12, 2014)
Funders 0

None

@article{Choi_2014, title={Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator}, volume={5}, ISSN={2041-1723}, url={http://dx.doi.org/10.1038/ncomms5881}, DOI={10.1038/ncomms5881}, number={1}, journal={Nature Communications}, publisher={Springer Science and Business Media LLC}, author={Choi, Sungkyu and Kim, Ye Ji and Kim, Sun Min and Yang, Jung Woon and Kim, Sung Wng and Cho, Eun Jin}, year={2014}, month=sep }