Fluorination of Organic Compounds Accompanied by Molecular Rearrangements

G. I. Borodkin; Бородкин Г. И.

doi:10.31857/S0514749225010017

Fluorination of Organic Compounds Accompanied by Molecular Rearrangements

作者: Borodkin G.I.¹
隶属关系:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
期: 卷 61, 编号 1 (2025)
页面: 5-44
栏目: ОБЗОРНАЯ СТАТЬЯ
URL: https://aspvestnik.ru/0514-7492/article/view/682042
DOI: https://doi.org/10.31857/S0514749225010017
EDN: https://elibrary.ru/AGHNMQ
ID: 682042

如何引用文章

全文:

开放存取

##reader.subscriptionAccessGranted##
受限制的访问

订阅存取

详细
全文:
作者简介
参考
补充文件
统计

详细

This literature review focuses on electrophilic and oxidative fluorination of organic compounds accompanied by molecular rearrangements. Special attention is given to the reaction mechanisms and selectivity issues.

关键词

fluorination, rearrangement, organic compounds, selectivity, reaction mechanism

全文:

作者简介

G. Borodkin

Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

编辑信件的主要联系方式.
Email: gibor@nioch.nsc.ru
俄罗斯联邦, 9, Acad. Lavrentiev Ave., Novosibirsk, 630090

参考

Zhou Y., Wang J., Gu Z., Wang S., Zhu W., Aceña J.L., Soloshonok V.F., Izawa K., Liu H. Chem. Rev. 2016, 116, 422–518. doi: 10.1021/acs.chemrev.5b00392
Lowe P.T., O’Hagan D. Chem. Soc. Rev. 2023, 52, 248–276. doi: 10.1039/d2cs00762b
Tiz D.B., Bagnoli L., Rosati O., Marini F., Sancineto L., Santi C. Molecules. 2022, 27, 1643–1666. doi: 10.3390/molecules27051643
Mei H., Han J., White S., Graham D.J., Izawa K., Sato T., Fustero S., Meanwell N.A., Soloshonok V.A. Chem. Eur. J. 2020, 26, 11349–11390. doi: 10.1002/chem.202000617
Dhiman P., Arora N., Thanikachalam P.V., Monga V. Bioorg. Chem. 2019, 92, 103291. doi: 10.1016/j.bioorg.2019.103291
Wang J., Sánchez-Roselló M., Aceña J.L., del Pozo C., Sorochinsky A.E., Fustero S., Soloshonok V.A., Liu H. Chem. Rev. 2014, 114, 2432–2506. doi: 10.1021/cr4002879
Zaikin P.A., Borodkin G.I. In: Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates. Ed. A. Postigo. Amsterdam: Elsevier. 2019, 105–135. doi: 10.1016/B978-0-12-812958-6.00003-3
Mykhailiuk P.K. Chem. Rev. 2021, 121, 1670–1715. D doi: 10.1021/acs.chemrev.0c01015
Jeschke P. Eur. J. Org. Chem. 2022, e202101513. doi: 10.1002/ejoc.202101513
Jeanmart S., Edmunds A.J.F., Lamberth C., Pouliot M. Bioorg. Med. Chem. 2016, 24, 317–341. doi: 10.1016/j.bmc.2015.12.014
Li F., Wang M., Liu S., Zhao Q. Chem. Sci., 2022, 13, 2184–2201. doi: 10.1039/d1sc06586f
Bremer M., Kirsch P., Klasen-Memmer M., Tarumi K. Angew. Chem. Int. Ed. 2013, 52, 8880–8896. doi: 10.1002/anie.201300903
Squeo B.M., Gregoriou V.G., Avgeropoulos A., Baysec S., Allardd S., Scherf U., Chochos C.L. Progress Polymer Sci. 2017, 71, 26–52. doi: 10.1016/j.progpolymsci.2017.02.003
Gillis E.P., Eastmann K.J., Hill M.D., Donnelly D.J., Meanwell N.A. J. Med. Chem. 2015, 58, 8315–8359. doi: 10.1021/acs.jmedchem.5b00258
Бородкин Г.И., Шубин В.Г. ЖОрХ, 2021, 57, 1209–1242 [Borodkin G.I., Shubin V.G. Russ. J. Org. Chem. 2021, 57, 1369–1397]. doi: 10.1134/S1070428021090013
Borodkin G.I., Shubin V.G. Chem. Heterocycl. Compd. 2022, 58, 84–96. doi: 10.1007/s10593-022-03060-3
Ramsden C.A. Arkivok 2014 (i), 109–126. doi: 10.3998/ark.5550190.p008.436
Бородкин Г.И., Шубин В.Г. Усп. хим., 2010, 79, 299–324. [Borodkin G.I., Shubin V.G. Russ. Chem. Rev. 2010, 79, 259–283]. doi: 10.1070/RC2010v079n04ABEH004091
Fluorination, Synthetic Organofluorine Chemistry. Eds. J. Hu, T. Umemoto, Springer Nature Singapore Pte Ltd. 2020, 429, 446, 451, 529, 558, 566. doi: 10.1007/978-981-10-3896-9
Бородкин Г.И. Усп. хим., 2023, 92, RCR5091 [Borodkin G.I. Russ. Chem. Rev. 2023, 92, RCR5091]. doi: 10.59761/RCR5091
Liang T., Neumann C.N., Ritter T. Angew. Chem. Int. Ed. 2013, 52, 8214–8264. doi: 10.1002/anie.201206566
Rozatian N., Hodgson D.R.W. Chem. Commun., 2021, 57, 683–712. doi: 10.1039/d0cc06339h
Sakthivel K., Subhiksha J., Raju A., Kumar R., Dohi T., Singha F.V. Arkivoc, 2022, 138–165. doi: 10.24820/ark.5550190.p011.996
Haufe G. Chem. Rec. 2023, 23, e202300140. doi: 10.1002/tcr.202300140
Borodkin G.I., Zaikin P.A., Shubin V.G. Tetrahedron Lett. 2006, 47, 2639–2642. doi: 10.1016/j.tetlet.2006.02.016
Бородкин Г.И., Заикин П.А., Шакиров М.М., Шубин В.Г. ЖОрХ, 2007, 43, 1460−1468 [Borodkin G.I., Zaikin P.A., Shakirov M.M., Shubin V.G. Russ. J. Org. Chem. 2007, 43, 1451−1459.] doi: 10.1134/S1070428007100077
Bykova T., Al-Maharik N., Slawin A.M.Z., O’Hagan D. J. Fluor. Chem. 2015, 179, 188–192. doi: 10.1016/j.jfluchem.2015.08.003
Kitamura T., Yoshida K., Mizuno S., Miyake A., Oyamada J. J. Org. Chem. 2018, 83, 14853–14860. doi: 10.1021/acs.joc.8b02473
Ilchenko N.O., Tasch B.O.A., Szabó K.J. Angew. Chem. Int. Ed. 2014, 53, 12897–12901. doi: 10.1002/anie.201408812
Banik S.M., Medley J.W., Jacobsen E.N. Science. 2016, 353, 51–54. doi: 10.1126/science.aaf8078
Zhou B., Haj M.K., Jacobsen E.N., Houk K.N., Xue X.-S. J. Am. Chem. Soc. 2018, 140, 15206−15218. doi: 10.1021/jacs.8b05935
Scheidt F., Neufeld J., Schäfer M., Thiehoff C., Gilmour R. Org. Lett. 2018, 20, 8073−8076. doi: 10.1021/acs.orglett.8b03794
Kitamura T., Muta K., Oyamada J. J. Org. Chem. 2015, 80, 10431−10436. doi: 10.1021/acs.joc.5b01929
Kitamura T., Kitamura D., Oyamada J., Higashi M., Kishikawa Y. Adv. Synth. Catal. 2023, 365, 2744–2750. doi: 10.1002/adsc.202300265
Lv W.-X., Li Q., Li J.-L., Li Z., Lin E., Tan D.-H., Cai Y.-H., Fan W.-X., Wang H. Angew. Chem. Int. Ed. 2018, 57, 16544–16548. doi: 10.1002/anie.201810204
Zhao Z., Racicot L., Murphy G.K. Angew. Chem. Int. Ed. 2017, 56, 11620–11623. doi: 10.1002/anie.201706798
Scheidt F., Schäfer M., Sarie J.C., Daniliuc C.G., Molloy J.J., Gilmour R. Angew. Chem. 2018, 130, 16431–16435. doi: 10.1002/ange.201810328
Sharma H.A., Mennie K.M., Kwan E.E., Jacobsen E.N. J. Am. Chem. Soc. 2020, 142, 16090– 16096.
Hoogesteger R.H., Murdoch N., Cordes D.B., Johns-ton C.P. Angew. Chem. Int. Ed. 2023, 62, e202308048. doi: 10.1002/anie.202308048
Wang Q., Biosca M., Himo F., Szabó K.J. Angew. Chem. Int. Ed. 2021, 60, 26327–26331. doi: 10.1002/anie.202109461
Scheidt F., Neufeld J., Schäfer M., Thiehoff C., Gil-mour R. Org. Lett. 2018, 20, 8073–8076. doi: 10.1021/acs.orglett.8b03794
Lin P.-P., Huang L.-L., Feng S.-X., Yang S., Wang H., Huang Z.-S., Li Q. Org. Lett. 2021, 23, 3088–3093. doi: 10.1021/acs.orglett.1c00767
Brunner C., Andries-Ulmer A., Kiefl G.M., Gulder T. Eur. J. Org. Chem. 2018, 2615–2621. doi: 10.1002/ejoc.201800129
Chai H., Zhen X., Wang X., Qi L., Qin Y., Xue J., Xu Z., Zhang H., Zhu W. ACS Omega, 2022, 7, 19988–19996.doi: 10.1021/acsomega.2c01791
Neufeld J., Stünkel T., Mück-Lichtenfeld C., Daniliuc C.G., Gilmour R. Angew. Chem. Int. Ed. 2021, 60, 13647–13651. doi: 10.1002/anie.202102222
Ulmer A., Brunner C., Arnold A.M., Pöthig A., Gulder T. Chem. Eur. J. 2016, 22, 3660–3664. doi: 10.1002/chem.201504749
Yan T., Zhou B., Xue X.-S., Cheng J.-P. J. Org. Chem. 2016, 81, 9006−9011. doi: 10.1021/acs.joc.6b01642
Geary G.C., Hope E.G., Stuart A.M. Angew. Chem. Int. Ed. 2015, 54, 14911–14914. doi: 10.1002/anie.201507790
Ren J., Du F.-H., Jia M.-C., Hu Z.-N., Chen Z., Zhang C. Angew. Chem. Int. Ed. 2021, 60, 24171–24178. doi: 10.1002/anie.202108589
Komatsuda M., Suto A., Kondo H., Takada H., Kato K., Saito B., Yamaguchi J. Chem. Sci., 2022, 13, 665–670. doi: 10.1039/d1sc06273e
Lin T.-S., Tsai W.-T., Liang P.-H. Tetrahedron 2016, 72, 5571–5577. doi: 10.1016/j.tet.2016.06.075
Xu Z.-F., Dai H., Shan L., Li C.-Y. Org. Lett. 2018, 20, 1054−1057. doi: 10.1021/acs.orglett.7b04014
Levin M.A., Ovian J.M., Read J.A., Sigman M.S., Jacobsen E.N. J. Am. Chem. Soc. 2020, 142, 14831–14837. doi: 10.1021/jacs.0c07043
Li C., Liao Y., Tan X., Liu X., Liu P., Lv W.-X., Wang H. Sci. China Chem., 2021, 64, 999–1003. doi: 10.1007/s11426-021-9965-9
Ning Y., Sivaguru P., Zanoni G., Anderson E.A., Bi X. Chem. 2020, 6, 486–496. doi: 10.1016/j.chempr.2019.12.004
Pang J.H., Chiba S. Sci. China Chem. 2020, 63, 1019–1020. doi: 10.1007/s11426-020-9773-3
Li H., Reddy B.R.P., Bi X. Org. Lett. 2019, 21, 9358–9362. doi: 10.1021/acs.orglett.9b03593
Inoue T., Nakabo S., Hara S. J. Fluor. Chem. 2016, 184, 22–27. doi: 10.1016/j.jfluchem.2016.02.002
Yang B., Chansaenpak K., Wu H., Zhu L., Wang M., Li Z., Lu H. Chem. Commun., 2017, 53, 3497–3500. doi: 10.1039/c7cc01393k
Ren S., Feng C., Loh T.-P. Org. Biomol. Chem., 2015, 13, 5105–5109. doi: 10.1039/c5ob00632e
Kim Y., Kim D.Y. Asian J. Org. Chem. 2019, 8, 679–682. doi: 10.1002/ajoc.201900029
Fan X., Wang Q., Wei Y., Shi M. Chem. Commun., 2018, 54, 10503–10506. doi: 10.1039/c8cc05634j
Garia A., Kumar S., Jain N. Asian J. Org. Chem. 2022, 11, e202200164. doi: 10.1002/ajoc.202200164
Liu A., Ni C., Xie Q., Hu J. Angew. Chem. Int. Ed. 2022, 61, e202115467. doi: 10.1002/anie.202115467
Romanov-Michailidis F., Guénée L., Alexakis A. Angew. Chem. Int. Ed. 2013, 52, 9266–9270. doi: 10.1002/anie.201303527
Romanov-Michailidis F., Romanova-Michaelides M., Pupier M., Alexakis A. Chem. Eur. J. 2015, 21, 5561–5583. doi: 10.1002/chem.201406133
Zhao P., Wang W., Gulder T. Org. Lett. 2023, 25, 6560−6565. doi: 10.1021/acs.orglett.3c02384
Feng S.-X., Yang S., Tu F.-H., Lin P.-P., Huang L.-L., Wang H., Huang Z.-S., Li Q. J. Org. Chem. 2021, 86, 6800−6812. doi: 10.1021/acs.joc.1c00578
Chen Z.-M., Yang B.-M., Chen Z.-H., Zhang Q.-W., Wang M., Tu Y.-Q. Chem. Eur. J. 2012, 18, 12950–12954. doi: 10.1002/chem.201202444
Das B.K., Tokunaga E., Harada K., Sumii Y., Shibata N. Org. Chem. Front., 2017, 4, 1726–1730. doi: 10.1039/c7qo00234c
Liao L., An R., Li H., Xu Y., Wu J.-J., Zhao X. Angew. Chem. Int. Ed. 2020, 59, 11010–11019. doi: 10.1002/anie.202003897
Alcaide B., Almendros P., Cembellıґn S., Martíґnez del Campo T., Muñoz A . Chem. Commun. 2016, 52, 6813–6816. doi: 10.1039/c6cc02012g
Lu Y., Kasahara A., Hyodo T., Ohara K., Yamaguchi K., Otani Y., Ohwada T. Org. Lett. 2023, 25, 3482–3486. doi: 10.1021/acs.orglett.3c01063
Thornbury R.T., Saini V., Fernandes T.A., Santiago C.B., Talbot E.P.A., Sigman M.S., McKenna J.M., Toste F.D. Chem. Sci. 2017, 8, 2890–2897. doi: 10.1039/c6sc05102b
Cao J., Wu H., Wang Q., Zhu J. Nature Chem. 2021, 13, 671–676. doi: 10.1038/s41557-021-00698-ydoi.org/10.1038/s41557-021-00698oi.org/10.1038/s41557-
Gong J., Wang Q., Zhu J. Angew. Chem. Int. Ed. 2022, 61, e202211470. doi: 10.1002/anie.202211470
Yang G., Wu H., Gallarati S., Corminboeuf C., Wang Q., Zhu J. J. Am. Chem. Soc. 2022, 144, 14047−14052. doi: 10.1021/jacs.2c06578
Mishra K., Singh J.B., Gupta T., Singh R.M. Org. Chem. Front. 2017, 4, 1794–1798. doi: 10.1039/c7qo00346c
De Haro T., Nevado C. Chem. Commun., 2011, 47, 248–249. doi: 10.1039/c002679d
Yang L., Ma Y., Song F., You J. Chem. Commun., 2014, 50, 3024–3026. doi: 10.1039/c3cc49851d
Liu N., Tian Q.-P., Yang Q., Yang S.-D. Synlett 2016, 27, 2621–2625. doi: 10.1055/s-0035-1562537; Art ID: st-2016-w0347-l
Bui T.T., Hong W.P., Kim H.-K. J. Fluor. Chem. 2021, 247, 109794. doi: 10.1016/j.jfluchem.2021.109794
Morcillo S.P. Angew. Chem. Int. Ed. 2019, 58, 14044–14054. doi: 10.1002/anie.201905218
Бородкин Г.И., Шубин В.Г. Усп. хим. 2019, 89, 160–203 [Borodkin G.I., Shubin V.G. Russ. Chem. Rev., 2019, 88, 160–203.] doi: 10.1070/RCR4833?locatt=label:RUSSIAN
Morcillo S.P., Dauncey E.M., Kim J.H., Douglas J.J., Sheikh N.S., Leonori D. Angew. Chem. Int. Ed. 2018, 57, 12945 –12949. doi: 10.1002/anie.201807941
Wang M.-M., Waser J. Angew. Chem. Int. Ed. 2020, 59, 16420–16424. doi: 10.1002/anie.202007864
Dauncey E.M., Morcillo S.P., Douglas J.J., Sheikh N.S., Leonori D. Angew. Chem. Int. Ed. 2018, 57, 744–748. doi: 10.1002/anie.201710790
Liu J., Wei Y., Shi M. Org. Chem. Front., 2021, 8, 94–100. doi: 10.1039/d0qo00853b