Recent Advances in the Chemistry and Application of SF₅-Compounds

Abstract

This review article outlines the literature from 2022 to 2024 covering developments in SF₅ chemistry. Recent synthetic methodologies of SF₅-containing building blocks are reported. These methods include the synthesis of SF₅Cl and its use in pentafluorosulfanylation reactions and oxidative fluorination reactions. Moreover, the reactivity of SF₅-alkynes as versatile platform to access new SF₅-compounds is described. Finally, the effects of the SF₅ moiety are highlighted according to its application in different fields, such as biological/medicinal chemistry, catalysis, and material sciences.

1 Introduction

2 Access to SF₅-Containing Building Blocks

2.1 By Means of SF₅Cl

2.1.1 Generation of SF₅Cl

2.2 By Means of Oxidative Fluorination

2.3 By Means of SF₅-Alkynes

2.4 Other Miscellaneous Aromatic and Aliphatic SF₅-Compounds

3 Applications

3.1 Medicinal and Biological Chemistry

3.2 Material Science

3.3 Catalysis

4 Conclusion

Key words

SF₅Cl - pentafluorosulfanylation - SF₅ building blocks - oxidative fluorination - medicinal chemistry - materials science - catalysis

Publikationsverlauf

Eingereicht: 08. Juli 2024

Angenommen nach Revision: 09. August 2024

Accepted Manuscript online:
09. August 2024

Artikel online veröffentlicht:
26. September 2024

• References

• 1 Haufe G. Tetrahedron 2022; 109: 132656
• 2 Saccomanno M, Hussain S, O’Connor NK, Beier P, Somlyay M, Konrat R, Murphy CD. Biodegradation 2018; 29: 259
• 3a Silvey GA, Cady GH. J. Am. Chem. Soc. 1950; 72: 3624
• 3b Roberts HL, Ray NH. J. Chem. Soc. 1960; 665
• 3c Sheppard WA. J. Am. Chem. Soc. 1960; 82: 4751
• 4 Ait-Mohand S, Dolbier WR. Org. Lett. 2002; 4: 3013
• 5 Savoie PR, Welch JT. Chem. Rev. 2015; 115: 1130
• 6a Sani M, Zanda M. Synthesis 2022; 54: 4184
• 6b Kordnezhadian R, Li B.-Y, Zogu A, Demaerel J, De Borggraeve WM, Ismalaj E. Chem. Eur. J. 2022; 28: e202201491
• 6c Magre M, Ni S, Cornella J. Angew. Chem. Int. Ed. 2022; 61: e202200904
• 6d Rombach D, Wagenknecht H.-A. Synthesis 2022; 54: 4883
• 6e Kraemer Y, Bergman EN, Togni A, Pitts CR. Angew. Chem. Int. Ed. 2022; 61: e202205088
• 7 Birepinte M, Champagne PA, Paquin J.-F. Angew. Chem. Int. Ed. 2022; 61: e202112575
• 8 Ouellet-Du Berger M.-R, Boucher M, Paquin J.-F. J. Fluorine Chem. 2023; 268: 11013
• 9 Shou J.-Y, Xu X.-H, Qing F.-L. J. Fluorine Chem. 2022; 261-262: 110018
• 10 Shou J.-Y, Xu X.-H, Qing F.-L. Angew. Chem. Int. Ed. 2021; 60: 15271
• 11 Shou J.-Y, Qing F.-L. Angew. Chem. Int. Ed. 2022; 61: e202208860
• 12 Nguyen TM, Legault CY, Blanchard N, Bizet V, Cahard D. Chem. Eur. J. 2023; 29: e202302914
• 13 Nguyen TM, Popek L, Matchavariani D, Blanchard N, Bizet V, Cahard D. Org. Lett. 2024; 26: 365
• 14 Wang L, Qin W. Org. Lett. 2024; 26: 5049
• 15 Kraemer Y, Ghiazza C, Ragan AN, Ni S, Lutz S, Neumann EK, Fettinger JC, Nöthling N, Goddard R, Cornella J, Pitts CR. Angew. Chem. Int. Ed. 2022; 61: e202211892
• 16 Zhao X, Shou J.-Y, Qing F.-L. Sci. China. Chem. 2023; 66: 2871
• 17 Kraemer K, Buldt JA, Kong W.-Y, Stephens AM, Ragan AN, Park S, Haidar ZC, Patel AH, Shey R, Dagan R, McLoughlin CP, Fettinger JC, Tantillo D, Pitts CR. Angew. Chem. Int. Ed. 2024; 63: e202319930
• 18 Wozniak M, Sander S, Cula B, Ahrens M, Braun T. Chem. Eur. J. 2022; 28: e202200626
• 19 Pitts CR, Santschi N, Togni A. WO 2019229103, 2019
• 20 Kordnezhadian R, De Bels T, Su K, Van Meervelt L, Ismalaj E, Demaerel J, De Borggraeve WM. Org. Lett. 2023; 25: 8947
• 21 Taponard A, Jarrosson T, Khrouz L, Médebielle M, Broggi J, Tlili A. Angew. Chem. Int. Ed. 2022; 61: e202204623
• 22a Umemoto T, Lloyd M, Garrick LM, Saito N. Beilstein J. Org. Chem. 2012; 8: 461
• 22b Pitts CR, Bornemann D, Liebing P, Santschi N, Togni A. Angew. Chem. Int. Ed. 2019; 58: 1950
• 22c Cui B, Kosobokov M, Matsuzaki K, Tokunaga E, Shibata N. Chem. Commun. 2017; 53: 5997
• 22d Wang L, Cornella J. Angew. Chem. Int. Ed. 2020; 59: 23510
• 22e Wang L, Ni S, Cornella J. Synthesis 2021; 53: 4308
• 23 Gatzenmeier T, Liu Y, Akamatsu M, Okazoe T, Nozaki K. ChemRxiv 2023; preprint
• 24 Kordnezhadian R, Zogu A, Borgarelli C, Van Lommel R, Demaerel J, De Borggraeve WM, Ismalaj E. Chem. Eur. J. 2023; 29: e202300361
• 25 Popek L, Nguyen TM, Blanchard N, Cahard D, Bizet V. Tetrahedron 2022; 117–118: 132814
• 26 Paquin P, DeGrâce N, Bélanger-Chabot G, Paquin J.-F. J. Org. Chem. 2024; 89: 3552
• 27 Popek L, Cabrera-Trujillo JJ, Debrauwer V, Blanchard N, Miqueu K, Bizet V. Angew. Chem. Int. Ed. 2023; 62: e202300685
• 28 Wenzel JO, Jester F, Togni A, Rombach D. Chem. Eur. J. 2024; 30: e202304015
• 29 Kucher H, Wenzel JO, Rombach D. ChemPlusChem 2024; 89: e202400168
• 30 Murata Y, Hada K, Aggarwal T, Escorihuela J, Shibata N. Angew. Chem. Int. Ed. 2024; 63: e202318086
• 31 Matchavariani D, Popek L, Cabrera-Trujillo JJ, Nguyen TM, Blanchard N, Miqueu K, Cahard D, Bizet V. Adv. Synth. Catal. 2024; 366: 3481
• 32 Köring L, Stepen A, Birenheide B, Barth S, Leskov M, Schoch R, Krämer F, Breher F, Paradies J. Angew. Chem. Int. Ed. 2023; 62: e202216959
• 33 Le TV, Daugulis O. Chem. Commun. 2022; 58: 537
• 34 Michaut A, Quatrevaux S, Queguiner L, Gaurrand S, Guillemont J. Lett. Org. Chem. 2022; 19: 602
• 35 Mastalerz V, Lam K, Paquin J.-F. J. Fluorine Chem. 2023; 268: 110113
• 36 Peyrical LC, Ouellet-Du Berger M.-R, Boucher M, Birepinte M, Paquin J.-F, Charette AB. Org. Lett. 2023; 25: 2487
• 37 Dudziński P, Matsnev AV, Trasher JS, Haufe G. J. Fluorine Chem. 2022; 264: 110051
• 38 Ghosh H, Bhattacharyya S, Schobert R, Dandawate P, Biersack B. Pharmaceutics 2023; 15: 1921
• 39 Kaps L, Klefenz A, Traenckner H, Schneider P, Andronache I, Schobert R, Biersack B, Schuppan D. Cells 2023; 12: 2619
• 40 Karaj E, Dlamini S, Koranne R, Sindi SH, Perera L, Taylor WR, Viranga Tillekeratne LM. Bioorg. Chem. 2022; 122: 105700
• 41 Scortichini M, Mohammed Idris R, Moschütz S, Keim A, Salmaso V, Dobelmann C, Oliva P, Losenkova K, Irjala H, Vaittinen S, Sandholm J, Yegutkin GG, Sträter N, Junker A, Müller CE, Jacobson KA. J. Med. Chem. 2022; 65: 2409
• 42 Pontikos MA, Leija C, Zhao Z, Wang X, Kilgore J, Tornesi B, Adenmatten N, Phillips M, Williams N. Biochem. Pharmacol. 2022; 204: 115237
• 43 Jose A, Guest D, LeGay R, Tizzard GJ, Coles SJ, Derveni M, Wright E, Marrison L, Lee AA, Morris A, Robinson M, von Delft F, Fearon D, Koekemoer L, Matviuk T, Aimon A, Schofiled CJ, Malla TR, London N, Greenland BW, Bagley MC, Spencer J. ChemMedChem 2022; 17: e2021006
• 44 Faber EB, Wang N, John K, Sun L, Wong HL, Burban D, Francis R, Tian D, Hong KH, Yang A, Wang L, Elsaid M, Khalid H, Levinson NM, Schonbrunn E, Hawkinson JE, Georg GI. J. Med. Chem. 2023; 66: 1928
• 45 Witoszka K, Malalinska J, Misicka A, Lipinski PF. J. ChemMedChem 2023; 18: e202300315
• 46 Toti KS, Pribut N, D’Erasmo M, Dasari M, Sharma SK, Bartsch PW, Burton SL, Gold HB, Bushnev A, Derdeyn CA, Basson AE, Liotta DC, Miller EJ. Front. Pharmacol. 2023; 13: 1083284
• 47 Salerno M, Varricchio C, Bevilacqua F, Jochmans D, Neyts J, Brancale A, Ferla S, Bassetto M. Eur. J. Med. Chem. 2023; 246: 114942
• 48a Naclerio GA, Abutaleb NS, Onyedibe KI, Seleem MN, Sintim HO. RSC Med. Chem. 2020; 11: 102
• 48b Naclerio GA, Onyedibe KI, Karanja CW, Aryal UK, Sintim HO. ACS Infect. Dis. 2022; 8: 865
• 49 Pormohammad A, Moradi M, Hommes JW, Pujol E, Naesens L, Vázquez S, Surewaard BG. J, Zarei M, Vazquez-Carrera M, Turner RJ. Microbiol. Spectrum 2024; 12: e00071-24
• 50 Shinya S, Kawai K, Kobayashi N, Karuo Y, Tarui A, Sato K, Otsuka M, Omote M. Bioorg. Med. Chem. 2024; 99: 117606
• 51a Onyedibe KI, Dayal N, Sintim HO. RSC Med. Chem. 2021; 12: 1879
• 51b Dayal N, Onyedibe KI, Gribble WM, Sintim HO. Eur. J. Med. Chem. 2022; 240: 114550
• 52 Liu R, Marshall K, Ma R, Lien Thi Pham K, Shetye G, Liu Z, Cho S, Jeong H, Franzblau SG, Moraski GC, Miller MJ. Bioorg. Chem. 2022; 128: 106074
• 53 Schubert TJ, Oboh E, Pekk H, Philo E, Teixeira JE, Stebbins EE, Miller P, Oliva J, Sverdrup FM, Griggs DW, Huston CD, Meyers MJ. J. Med. Chem. 2023; 66: 7834
• 54 Granberg KL, Sakamaki S, Fuchigami R, Niwa Y, Fujio M, Kato H, Bergström F, Larsson N, Persson M, Villar IC, Fujita T, Sugikawa E, Althage M, Yano N, Yokoyama Y, Kimura J, Lal M, Mochida H. J. Med. Chem. 2024; 67: 4442
• 55 MacDerott-Opeskin H, Clarke C, Wu X, Roseblade A, York E, Pacchini E, Roy R, Cranfield C, Gale PA, O’Mara ML, Murray M, Rawling T. Org. Biomol. Chem. 2023; 21: 132
• 56 Kadakia RT, Ryan RT, Cooke DJ, Que EL. Chem. Sci. 2023; 14: 5099
• 57 Hiscocks HG, Pascali G, Ung AT. AppliedChem 2023; 3: 256
• 58 Xie Y, Iwata J, Matsumoto T, Yamada NL, Nemoto F, Seto H, Nishino T. Langmuir 2022; 38: 6472
• 59 James RD, Cucinotta F, Waddell PG, Benniston AC. New J. Chem. 2023; 47: 8451
• 60 James RD, Alqahtani LS, Mallows J, Flint HV, Waddell PG, Woodford OJ, Gibson EA. Sustainable Energy Fuels 2023; 7: 1494
• 61 Gao H, Sevilla AR, Hobold GM, Melemed AM, Guo R, Jones SC, Gallant BM. Proc. Natl. Acad. Sci. U. S. A. 2022; 119: e2121440119
• 62 Sevilla AR, Gao H, Steinberg KJ, Gallant BM. J. Phys. Chem. C 2023; 127: 1722
• 63 Doyle LR, Thomson EA, Burnage AL, Whitwood AC, Jenkins HT, Macgregor SA, Weller AS. Dalton Trans. 2022; 51: 3661
• 64 Liu Y, Zeplichal M, Katzbach S, Wiesner A, Das S, Terfort A, Zharnikov M. Nano Res. 2023; 16: 7991
• 65 Jelínková V, Dellai A, Vachtlová M, Fecková M, Podlesný J, Klikar M, Castet F, Růžička A, Pařík P, Pytela O, Bureš F. J. Photochem. Photobiol., A 2024; 449: 115390
• 66 Ghosh S, Erchinger JE, Maji R, List B. J. Am. Chem. Soc. 2022; 144: 6703
• 67 Tsuji N, Sidorov P, Zhu C, Nagata Y, Gimadiev T, Varnek A, List B. Angew. Chem. Int. Ed. 2023; 62: e202218659
• 68 Boddy AJ, Sahay AK, Rivers EL, White AJ. P, Spivey AC, Bull JA. Org. Lett. 2024; 26: 2079