Abstract
Fluoroalkyl iodides are convenient sources of fluoroalkyl radicals under photocatalytic conditions. After the addition of a fluorine radical to a double bond, the resulting radical can react in several directions, including abstraction of an iodine atom from the starting iodide, abstraction of a hydrogen atom from a reducing agent, intramolecular interception by an aromatic system, and one-electron oxidation. These reactions make it possible to obtain a wide range of organofluorine compounds. The review summarizes data for the last five years.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Election of the Full Members (Academicians), Corresponding Members, and Foreign Members of the Russian Academy of Sciences, Russ. Chem. Bull., 2022, 71, 1559; DOI: https://doi.org/10.1007/s11172-022-3565-4.
M. Inoue, Y. Sumii, N. Shibata, ACS Omega, 2020, 5, 10633–10640; DOI: https://doi.org/10.1021/acsomega.0c00830.
N. A. Meanwell, J. Med. Chem., 2018, 61, 5822–5880; DOI: https://doi.org/10.1021/acs.jmedchem.7b01788.
J. Han, A. M. Remete, L. S. Dobson, L. Kiss, K. Izawa, H. Moriwaki, V. A. Soloshonok, D. O’Hagan, J. Fluorine Chem., 2020, 239, 109639; DOI: https://doi.org/10.1016/j.jfluchem.2020.109639.
B. M. Johnson, Y.-Z. Shu, X. Zhuo, N. A. Meanwell, J. Med. Chem., 2020, 63, 6315–6386; DOI: https://doi.org/10.1021/acs.jmedchem.9b01877.
I. B. Chernikova, M. S. Yunusov, Russ. Chem. Bull., 2022, 71, 1; DOI: https://doi.org/10.1007/s11172-022-3370-0.
Y. Ogawa, E. Tokunaga, O. Kobayashi, K. Hirai, N. Shibata, iScience, 2020, 23, 101467; DOI: https://doi.org/10.1016/j.isci.2020.101467.
M. Beller, F. Fischer, A. Locher, H. Neumann, C. Taeschler, F. Ye, S. Zhang, Chimia, 2021, 75, 923; DOI: https://doi.org/10.2533/chimia.2021.923.
X.-H. Liu, J. Leng, S.-J. Jia, J.-H. Hao, F. Zhang, H.-L. Qin, C.-P. Zhang, J. Fluorine Chem., 2016, 189, 59–67; DOI: https://doi.org/10.1016/j.jfluchem.2016.07.021.
G. Dagousset, A. Carboni, G. Masson, E. Magnier, in Modern Synthesis Processes and Reactivity of Fluorinated Compounds, Eds H. Groult, F. R. Leroux, A. Tressaud, Elsevier, 2017, pp. 389–426.
S. Barata-Vallejo, M. V. Cooke, A. Postigo, ACS Catal., 2018, 8, 7287–7307; DOI: https://doi.org/10.1021/acscatal.8b02066.
T. Chatterjee, N. Iqbal, Y. You, E. J. Cho, Acc. Chem. Res., 2016, 49, 2284–2294; DOI: https://doi.org/10.1021/acs.accounts.6b00248.
W. R. Dolbier, Chem. Rev., 1996, 96, 1557–1584; DOI: https://doi.org/10.1021/cr941142c.
E. V. Tretyakov, P. A. Fedyushin, Russ. Chem. Bull., 2021, 70, 2298; DOI: https://doi.org/10.1007/s11172-021-3346-5.
M. H. Shaw, J. Twilton, D. W. C. MacMillan, J. Org. Chem., 2016, 81, 6898–6926; DOI: https://doi.org/10.1021/acs.joc.6b01449.
I. Ghosh, L. Marzo, A. Das, R. Shaikh, B. Koenig, Acc. Chem. Res., 2016, 49, 1566–1577; DOI: https://doi.org/10.1021/acs.accounts.6b00229.
D. M. Schultz, T. P. Yoon, Science, 2014, 343, 1239176; DOI: https://doi.org/10.1126/science.1239176.
J. W. Tucker, C. R. J. Stephenson, J. Org. Chem., 2012, 77, 1617–1622; DOI: https://doi.org/10.1021/jo202538x.
N. O. Brace, J. Fluorine Chem., 1999, 93, 1–25; DOI: https://doi.org/10.1016/S0022-1139(98)00255-3.
F. Juliá, T. Constantin, D. Leonori, Chem. Rev., 2022, 122, 2292–2352; DOI: https://doi.org/10.1021/acs.chemrev.1c00558.
J. M. Munoz-Molina, T. R. Belderrain, P. J. Perez, Eur. J. Inorg. Chem., 2011, 2011, 3155–3164; DOI: https://doi.org/10.1002/ejic.201100379.
J. D. Nguyen, J. W. Tucker, M. D. Konieczynska, C. R. J. Stephenson, J. Am. Chem. Soc., 2011, 133, 4160–4163; DOI: https://doi.org/10.1021/ja108560e.
C.-J. Wallentin, J. D. Nguyen, P. Finkbeiner, C. R. J. Stephenson, J. Am. Chem. Soc., 2012, 134, 8875–8884; DOI: https://doi.org/10.1021/ja300798k.
M. Kublicki, M. Dąbrowski, K. Durka, T. Kliś, J. Serwatowski, K. Woźniak, Tetrahedron Lett., 2017, 58, 2162–2165; DOI: https://doi.org/10.1016/j.tetlet.2017.04.075.
M. Kublicki, K. Durka, T. Kliś, Tetrahedron Lett., 2018, 59, 2700–2703; DOI: https://doi.org/10.1016/j.tetlet.2018.05.086.
M. Huang, L. Li, Z.-G. Zhao, Q.-Y. Chen, Y. Guo, Synthesis, 2015, 47, 3891–3900; DOI: https://doi.org/10.1055/s-0035-1560260.
S. Kim, G. Park, E. J. Cho, Y. You, J. Org. Chem., 2016, 81, 7072–7079; DOI: https://doi.org/10.1021/acs.joc.6b00966.
K. Matsuzaki, T. Hiromura, E. Tokunaga, N. Shibata, ChemistryOpen, 2017, 6, 226–230; DOI: https://doi.org/10.1002/open.201600172.
T. Yajima, M. Ikegami, Eur. J. Org. Chem., 2017, 2017, 2126–2129; DOI: https://doi.org/10.1002/ejoc.201700077.
M. Kublicki, B. Ogonowski, D. Wieczorkowski, K. Durka, T. Kliś, Tetrahedron Lett., 2019, 60, 1918–1923; DOI: https://doi.org/10.1016/j.tetlet.2019.06.032.
C. Rosso, G. Filippini, P. G. Cozzi, A. Gualandi, M. Prato, ChemPhotoChem, 2019, 3, 193–197; DOI: https://doi.org/10.1002/cptc.201900018.
C. Rosso, J. D. Williams, G. Filippini, M. Prato, C. O. Kappe, Org. Lett., 2019, 21, 5341–5345; DOI: https://doi.org/10.1021/acs.orglett.9b01992.
N. Iqbal, S. Choi, E. Kim, E. J. Cho, J. Org. Chem., 2012, 77, 11383–11387; DOI: https://doi.org/10.1021/jo3022346.
W. J. Choi, S. Choi, K. Ohkubo, S. Fukuzumi, E. J. Cho, Y. You, Chem. Sci., 2015, 6, 1454–1464; DOI: https://doi.org/10.1039/C4SC02537G.
R. Adamik, T. Földesi, Z. Novák, Org. Lett., 2020, 22, 8091–8095; DOI: https://doi.org/10.1021/acs.orglett.0c03043.
J. Moon, Y. K. Moon, D. D. Park, S. Choi, Y. You, E. J. Cho, J. Org. Chem., 2019, 84, 12925–12932; DOI: https://doi.org/10.1021/acs.joc.9b01624.
D. P. Tiwari, S. Dabral, J. Wen, J. Wiesenthal, S. Terhorst, C. Bolm, Org. Lett., 2017, 19, 4295–4298; DOI: https://doi.org/10.1021/acs.orglett.7b01952.
G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, G. Terraneo, Chem. Rev., 2016, 116, 2478–2601; DOI: https://doi.org/10.1021/acs.chemrev.5b00484.
C. G. S. Lima, T. de M. Lima, M. Duarte, I. D. Jurberg, M. W. Paixão, ACS Catal., 2016, 6, 1389–1407; DOI: https://doi.org/10.1021/acscatal.5b02386.
Y. Wang, J. Wang, G.-X. Li, G. He, G. Chen, Org. Lett., 2017, 19, 1442–1445; DOI: https://doi.org/10.1021/acs.orglett.7b00375.
T. Mao, M.-J. Ma, L. Zhao, D.-P. Xue, Y. Yu, J. Gu, C.-Y. He, Chem. Commun., 2020, 56, 1815–1818; DOI: https://doi.org/10.1039/c9cc09517a.
L. I. Panferova, M. I. Struchkova, A. D. Dilman, Synthesis, 2017, 49, 4124–4132; DOI: https://doi.org/10.1055/s-0036-1590855.
L. I. Panferova, M. I. Struchkova, A. D. Dilman, Eur. J. Org. Chem., 2018, 3834–3836; DOI: DOI: https://doi.org/10.1002/ejoc.201800543.
M. D. Kosobokov, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett., 2014, 16, 3784–3787; DOI: https://doi.org/10.1021/ol501674n.
V. V. Levin, V. O. Smirnov, M. I. Struchkova, A. D. Dilman, J. Org. Chem., 2015, 80, 9349–9353; DOI: https://doi.org/10.1021/acs.joc.5b01590.
L. I. Panferova, V. V. Levin, M. I. Struchkova, A. D. Dilman, Chem. Commun., 2019, 55, 1314–1317; DOI: https://doi.org/10.1039/c8cc09115c.
C.-M. Hu, Y.-L. Qiu, Tetrahedron Lett., 1991, 32, 4001–4002; DOI: https://doi.org/10.1016/0040-4039(91)80611-9.
V. I. Supranovich, V. V. Levin, M. I. Struchkova, J. Hu, A. D. Dilman, Beilstein J. Org. Chem., 2018, 14, 1637–1641; DOI: https://doi.org/10.3762/bjoc.14.139.
T. Kawamoto, I. Ryu, Org. Biomol. Chem., 2014, 12, 9733–9742; DOI: https://doi.org/10.1039/c4ob01784f.
V. I. Supranovich, V. V. Levin, M. I. Struchkova, A. A. Korlyukov, A. D. Dilman, Org. Lett., 2017, 19, 3215–3218; DOI: https://doi.org/10.1021/acs.orglett.7b01334.
N. J. W. Straathof, S. E. Cramer, V. Hessel, T. Noël, Angew. Chem., Int. Ed., 2016, 55, 15549–15553; DOI: https://doi.org/10.1002/anie.201608297.
S. M. Hell, C. F. Meyer, S. Ortalli, J. B. I. Sap, X. Chen, V. Gouverneur, Chem. Sci., 2021, 12, 12149–12155; DOI: https://doi.org/10.1039/D1SC03421A.
X. Ren, X. Gao, Q.-Q. Min, S. Zhang, X. Zhang, Chem. Sci., 2022, 13, 3454–3460; DOI: https://doi.org/10.1039/D1SC07061D.
Z. Li, M. Wang, Z. Shi, Angew. Chem., Int. Ed., 2021, 60, 186–190; DOI: https://doi.org/10.1002/anie.202010839.
S. Tang, L. Yuan, Y.-L. Deng, Z.-Z. Li, L.-N. Wang, G.-X. Huang, R.-L. Sheng, Tetrahedron Lett., 2017, 58, 329–332; DOI: https://doi.org/10.1016/j.tetlet.2016.12.027.
Z. Yang, A. Tang, Synlett, 2019, 30, 1061–1066; DOI: https://doi.org/10.1055/s-0037-1611781.
S. Tang, L. Yuan, Z.-Z. Li, Z.-Y. Peng, Y.-L. Deng, L.-N. Wang, G.-X. Huang, R.-L. Sheng, Tetrahedron Lett., 2017, 58, 2127–2130; DOI: https://doi.org/10.1016/j.tetlet.2017.04.055.
Author information
Authors and Affiliations
Corresponding authors
Additional information
No human or animal subjects were used in this research.
The authors declare no competing interests.
Dilman Alexander Davidovich, born in 1976, Doctor of Chemical Sciences, Professor of the Russian Academy of Sciences, Deputy Director for Research at the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences (Moscow), an expert in the field of photocatalysis in organic and organofluorine chemistry, was elected a member correspondent of the Russian Academy of Sciences in 2022 (more detailed information is given in Ref. 1).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 1, pp. 61–72, January, 2023.
Rights and permissions
About this article
Cite this article
Chernov, G.I., Levin, V.V. & Dilman, A.D. Photocatalytic reactions of fluoroalkyl iodides with alkenes. Russ Chem Bull 72, 61–72 (2023). https://doi.org/10.1007/s11172-023-3714-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-023-3714-4