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DOI: 10.1055/a-2435-5669
The First Decade of SuFEx Chemistry: Advancements in SuFEx Polymerization, Non-Canonical SuFEx Reactions, and SuFEx Radiochemistry


Abstract
This year marks the 10th anniversary of SuFEx chemistry, a field that has witnessed significant advancements over the past decade. These include efficient synthetic strategies toward polymerization via the SuFEx approach leading to diverse polymers, alongside the discovery of new SuFExable hubs and coupling conditions. Non-canonical reactions, such as deoxyfluorination and on-water reactions, have also emerged. Furthermore, there have been substantial strides in the radiosynthesis of [18F] SuFExable hubs. This review provides an overview of these developments, focusing on polymerization, non-canonical reaction, and radiochemistry in SuFEx chemistry.
1 Introduction
2 SuFEx Polymerization
3 Non-Canonical SuFEx Reactions
4 Fluorine-18 SuFEx Radiochemistry
5 Conclusions and Outlook
Key words
SuFEx chemistry - polymerization - polymer degradation - deoxyhalogenation - radiofluorinationPublikationsverlauf
Eingereicht: 07. August 2024
Angenommen nach Revision: 07. Oktober 2024
Accepted Manuscript online:
07. Oktober 2024
Artikel online veröffentlicht:
11. November 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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References
- 1 Dong J, Krasnova L, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2014; 53: 9430
- 2 Smedley CJ, Homer JA, Gialelis TL, Barrow AS, Koelln RA, Moses JE. Angew. Chem. Int. Ed. 2022; 61: e202112375
- 3 Homer JA, Koelln RA, Barrow AS, Gialelis TL, Boiarska Z, Steinohrt NS, Lee EF, Yang W.-H, Johnson RM, Chung T, Habowski AN, Vishwakarma DS, Bhunia D, Avanzi C, Moorhouse AD, Jackson M, Tuveson DA, Lyons SK, Lukey MJ, Fairlie WD, Haider SM, Steinmetz MO, Prota AE, Moses JE. Chem. Sci. 2024; 15: 3879
- 4 Kim WG, Kang ME, Lee JB, Jeon MH, Lee S, Lee J, Cho B, Cal PM. S. D, Kang S, Kee J.-M, Bernardes GJ. L, Rohde J.-U, Choe W, Hong SY. J. Am. Chem. Soc. 2017; 139: 12121
- 5 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 6 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
- 7 Saraswat SK, Seemaladinne R, Abdullah MN, Zaini H, Ahmad N, Ahmad N, Vessally E. RSC Adv. 2023; 13: 13642
- 8 Na J.-H, Liu X, Jing J.-W, Wang J, Chu X.-Q, Ma M, Xu H, Zhou X, Shen Z.-L. Org. Lett. 2023; 25: 2318
- 9 Barrow AS, Smedley CJ, Zheng Q, Li S, Dong J, Moses JE. Chem. Soc. Rev. 2019; 48: 4731
- 10 Chinthakindi PK, Kruger HG, Govender T, Naicker T, Arvidsson PI. J. Org. Chem. 2016; 81: 2618
- 11 Lou TS.-B, Willis MC. Nat. Rev. Chem. 2022; 6: 146
- 12 Zheng Q, Xu H, Wang H, Du W.-GH, Wang N, Xiong H, Gu Y, Noodleman L, Sharpless KB, Yang G, Wu P. J. Am. Chem. Soc. 2021; 143: 3753
- 13 Guo T, Meng G, Zhan X, Yang Q, Ma T, Xu L, Sharpless KB, Dong J. Angew. Chem. Int. Ed. 2018; 57: 2605
- 14 Paioti PH. S, Lounsbury KE, Romiti F, Formica M, Bauer V, Zandonella C, Hackey ME, del Pozo J, Hoveyda AH. Nat. Chem. 2024; 16: 426
- 15 Ren X, Guo C, Li X, Wu Y, Zhang Y, Li S, Zhang K. Macromolecules 2023; 56: 1045
- 16 Li Z, Ren X, Sun P, Ding H, Li S, Zhao Y, Zhang K. ACS Macro Lett. 2021; 10: 223
- 17 Yang C, Flynn JP, Niu J. Angew. Chem. Int. Ed. 2018; 57: 16194
- 18 Schnaider L, Tan S, Singh PR, Capuano F, Scott AJ, Hambley R, Lu L, Yang H, Wallace EJ, Jo H, DeGrado WF. J. Am. Chem. Soc. 2024; 146: 25047
- 19 Qin Z, Zhang K, He P, Zhang X, Xie M, Fu Y, Gu C, Zhu Y, Tong A, Wei H, Zhang C, Xiang Y. Nat. Chem. 2023; 15: 1705
- 20 Yang L, Yuan Z, Li Y, Yang S, Yu B. Med. Chem. Res. 2024; 33: 1315
- 21 Deng X, Zhu X. ACS Omega 2023; 8: 37720
- 22 Yang G, Huang Z, Majeed I, Fan C, Lu J, Wang K, Fan W, Zhao J, Zeng Z. J. Mater. Chem. A 2024; 12: 10242
- 23 Moon H, Nam H, Kim MP, Lee SM, Kim H, Jeon MH, Lee YS, Kim K, Chun JH, Kwak SK, Hong SY, Choi NS. Adv. Funct. Mater. 2023; 33: 2303029
- 24 Homer JA, Xu L, Kayambu N, Zheng Q, Choi EJ, Kim BM, Sharpless KB, Zuilhof H, Dong J, Moses JE. Nat. Rev. Methods Primers 2023; 3: 58
- 25 Zeng D, Deng W.-P, Jiang X. Chem. Eur. J. 2023; 29: e202300536
- 26 Zeng D, Deng W.-P, Jiang X. Natl. Sci. Rev. 2023; 10: nwad123
- 27 Lucas SW, Qin RZ, Rakesh KP, Sharath Kumar KS, Qin H.-L. Bioorg. Chem. 2023; 130: 106227
- 28 Lee C, Cook AJ, Elisabeth JE, Friede NC, Sammis GM, Ball ND. ACS Catal. 2021; 11: 6578
- 29 Firth WC. J. Polym. Sci., Part B: Polym. Phys. 1972; 10: 637
- 30 Work JL, Herweh JE. J. Polym. Sci., Part A-1: Polym. Chem. 1968; 6: 2022
- 31 Dong J, Sharpless KB, Kwisnek L, Oakdale JS, Fokin VV. Angew. Chem. Int. Ed. 2014; 53: 9466
- 32 Gembus V, Marsais F, Levacher V. Synlett 2008; 1463
- 33 Scroggie KR, Perkins MV, Chalker JM. Front. Chem. 2021; 9: 687678
- 34 Wang H, Zhou F, Ren G, Zheng Q, Chen H, Gao B, Klivansky L, Liu Y, Wu B, Xu Q, Lu J, Sharpless KB, Wu P. Angew. Chem. Int. Ed. 2017; 56: 11203
- 35 Starks CM, Liotta CL, Halpern ME. Phase-Transfer Catalysis, 1st ed. Springer; Dordrecht: 1994: 1
- 36 Gao B, Zhang L, Zheng Q, Zhou F, Klivansky LM, Lu J, Liu Y, Dong J, Wu P, Sharpless KB. Nat. Chem. 2017; 9: 1083
- 37 Kim H, Zhao J, Bae J, Klivansky LM, Dailing EA, Liu Y, Cappiello JR, Sharpless KB, Wu P. ACS Cent. Sci. 2021; 7: 1919
- 38 Li S, Wu P, Moses JE, Sharpless KB. Angew. Chem. Int. Ed. 2017; 56: 2903
- 39 Kim MP, Kayal S, Hwang C, Bae J, Kim H, Hwang DG, Jeon MH, Seo JK, Ahn D, Lee W, Seo S, Chun J.-H, Yu Y, Hong SY. Nat. Commun. 2024; 15: 3381
- 40 Kulow RW, Wu JW, Kim C, Michaudel Q. Chem. Sci. 2020; 11: 7807
- 41 Wu JW, Kulow RW, Redding MJ, Fine AJ, Grayson SM, Michaudel Q. ACS Polym. Au 2023; 3: 259
- 42 Li S, Li G, Gao B, Pujari SP, Chen X, Kim H, Zhou F, Klivansky LM, Liu Y, Driss H, Liang D.-D, Lu J, Wu P, Zuilhof H, Moses J, Sharpless KB. Nat. Chem. 2021; 13: 858
- 43 Liang D.-D, Pujari SP, Subramaniam M, Besten M, Zuilhof H. Angew. Chem. Int. Ed. 2022; 61: e202116158
- 44 Yatvin J, Brooks K, Locklin J. Angew. Chem. Int. Ed. 2015; 54: 13370
- 45 Oakdale JS, Kwisnek L, Fokin VV. Macromolecules 2016; 49: 4473
- 46 Wu J, Wan H, Zhou S, Gu P, Zhu Y, Xu Q, Lu J. Chem. Asian J. 2021; 16: 3202
- 47 Briceno ES, Stephen K, Hobbs CE. J. Polym. Sci. 2023; 61: 94
- 48 Li M, Ma J.-A, Liao S. Macromolecules 2023; 56: 806
- 49 Jehanno C, Alty JW, Roosen M, De Meester S, Dove AP, Chen EY.-X, Leibfarth FA, Sardon H. Nature 2022; 603: 803
- 50 Cao Z, Zhou F, Gu P.-Y, Chen D, He J, Cappiello JR, Wu P, Xu Q, Lu J. Polym. Chem. 2020; 11: 3120
- 51 Darwish D, Noreyko J. Can. J. Chem. 1965; 43: 1366
- 52 Szeler K, Williams NH, Hengge AC, Kamerlin SC. L. J. Org. Chem. 2020; 85: 6489
- 53 Younker JM, Hengge AC. J. Org. Chem. 2004; 69: 9043
- 54 Gnanou Y, Fontanille M. Organic and Physical Chemistry of Polymers, 1st ed. John Wiley & Sons; Hoboken: 2007: 357
- 55 Gopferich A. Biomaterials 1996; 17: 103
- 56 Bialk-Bielinska A, Stolte S, Matzke M, Fabianska A, Maszkowska J, Kolodziejska M, Liberek B, Stepnowski P, Kumirska J. J. Hazard. Mater. 2012; 221–222: 264
- 57 Searles S, Nukina S. Chem. Rev. 1959; 59: 1077
- 58 Perovich GL, Kazachenko VP, Strakhova NN, Raevsky OA. J. Chem. Eng. Data 2014; 59: 4217
- 59 Chao Y, Krishna A, Subramaniam M, Liang DD, Pujari SP, Sue AC. H, Li G, Miloserdov FM, Zuilhof H. Angew. Chem. Int. Ed. 2022; 61: e202207456
- 60 Xiao X, Zhou F, Jiang J, Chen H, Wang L, Chen D, Xu Q, Lu J. Polym. Chem. 2018; 9: 1040
- 61 Wang M, Jin H.-S, Chen X.-M, Lin B.-P, Yang H. Polym. Chem. 2019; 10: 3657
- 62 Wan H, Zhou S, Gu P, Zhou F, Lyu D, Xu Q, Wang A, Shi H, Xu Q, Lu J. Polym. Chem. 2020; 11: 1033
- 63 Wan H, Xu Q, Wu J, Lian C, Liu H, Zhang B, He J, Chen D, Lu J. Angew. Chem. Int. Ed. 2022; 61: e202208577
- 64 Wang Z.-P, Zhou J.-Y, Liu Q, Hou C, Xie S, Yin M.-J, An Q.-F. J. Membr. Sci. 2022; 664: 121088
- 65 Li H, Chang BS, Kim H, Xie Z, Lainé A, Ma L, Xu T, Yang C, Kwon J, Shelton SW, Klivansky LM, Altoé V, Gao B, Schwartzberg AM, Peng Z, Ritchie RO, Xu T, Salmeron M, Ruiz R, Sharpless KB, Wu P, Liu Y. Joule 2023; 7: 95
- 66 Arpe H.-J. Industrial Organic Chemistry, 5th ed. Wiley-VCH; Weinheim: 2010
- 67 Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
- 68 Umemoto T, Singh RP, Xu Y, Saito N. J. Am. Chem. Soc. 2010; 132: 18199
- 69 Beaulieu F, Beauregard L.-P, Courchesne G, Couturier M, LaFlamme F, L’Heureux A. Org. Lett. 2009; 11: 5050
- 70 Lal GS, Pez GP, Pesaresi RJ, Prozonic FM. Chem. Commun. 1999; 215
- 71 Middleton WJ. J. Org. Chem. 1975; 40: 574
- 72 Singh RP, Shreeve JM. Synthesis 2002; 2561
- 73 Nielsen MK, Ugaz CR, Li W, Doyle AG. J. Am. Chem. Soc. 2015; 137: 9571
- 74 Lee C, Lai J, Epifanov M, Wang CX, Sammis GM. J. Fluorine Chem. 2021; 251: 109888
- 75 Wang X, Zhou M, Liu Q, Ni C, Fei Z, Li W, Hu J. Chem. Commun. 2021; 57: 8170
- 76 Odoh AS, Keeler C, Kim B. Org. Lett. 2024; 26: 4013
- 77 Mo JY, Epifanov M, Hodgson JW, Dubois R, Sammis GM. Chem. Eur. J. 2020; 26: 4958
- 78 Swallow S. Prog. Med. Chem. 2015; 54: 65
- 79 Epifanov M, Foth PJ, Gu F, Barrillon C, Kanani SS, Higman CS, Hein JE, Sammis GM. J. Am. Chem. Soc. 2018; 140: 16464
- 80 Santos L, Audet F, Donnard M, Panossian A, Vors J.-P, Bernier D, Pazenok S, Leroux FR. Chem. Eur. J. 2023; 29: e202300792
- 81 Foth PJ, Gu F, Bolduc TG, Kanani SS, Sammis GM. Chem. Sci. 2019; 10: 10331
- 82 Tang P, Wang W, Ritter T. J. Am. Chem. Soc. 2011; 133: 11482
- 83 Schimler SD, Cismesia MA, Hanley PS, Froese RD. J, Jansma MJ, Bland DC, Sanford MS. J. Am. Chem. Soc. 2017; 139: 1452
- 84 Schimler SD, Froese RD. J, Bland DC, Sanford MS. J. Org. Chem. 2018; 83: 11178
- 85 Chattapadhyay D, Aydogan A, Doktor K, Maity A, Wu JW, Michaudel Q. ACS Catal. 2023; 13: 7263
- 86 Liang Q, Xing P, Huang Z, Dong J, Sharpless KB, Li X, Jiang B. Org. Lett. 2015; 17: 1942
- 87 Hanley PS, Krasovskiy AL, Ober MS, Whiteker GT, Kruper WJ. ACS Catal. 2015; 5: 5041
- 88 Sahoo MK, Lee JW, Lee S, Choe W, Jung B, Kwak J, Hong SY. JACS Au 2024; 4: 1646
- 89 Park JH, Lee SB, Koo BJ, Bae HY. ChemSusChem 2022; 15: e202201000
- 90 Lee SB, Park JH, Bae HY. ChemSusChem 2022; 15: e202200634
- 91 Kim SB, Kim DH, Bae HY. Nat. Commun. 2024; 15: 3876
- 92 Ametamey SM, Honer M, Schubiger PA. Chem. Rev. 2008; 108: 1501
- 93 Cai L, Lu S, Pike VW. Eur. J. Org. Chem. 2008; 2008: 2853
- 94 Khoshnevisan A, Chuamsaamarkkee K, Boudjemeline M, Jackson A, Smith GE, Gee AD, Fruhwirth GO, Blower PJ. J. Nucl. Med. 2017; 58: 156
- 95 Kwon Y.-D, Jeon MH, Park NK, Seo JK, Son J, Ryu YH, Hong SY, Chun J.-H. Org. Lett. 2020; 22: 5511
- 96 Kim MP, Cho H, Kayal S, Jeon MH, Seo JK, Son J, Jeong J, Hong SY, Chun J.-H. J. Org. Chem. 2023; 88: 6263
- 97 Battisti UM, Müller M, García-Vázquez R, Herth MM. Synlett 2023; 34: A
- 98 Jeon MH, Kwon Y.-D, Kim MP, Torres GB, Seo JK, Son J, Ryu YH, Hong SY, Chun J.-H. Org. Lett. 2021; 23: 2766