Recent Advances in the Synthesis and Medicinal Chemistry of SF5 and SF4Cl Compounds

Monica Sani; Matteo Zanda

doi:10.1055/a-1845-9291

Synthesis, Table of Contents

Synthesis 2022; 54(19): 4184-4209
DOI: 10.1055/a-1845-9291

short review

Recent Advances in the Synthesis and Medicinal Chemistry of SF₅ and SF₄Cl Compounds

Monica Sani∗

,

Matteo Zanda

Abstract

All articles of this category

Abstract

This short review covers the most important advances published in the literature during the last five years, concerning the synthesis, chemical modifications, and applications of SF₅ and SF₄Cl compounds in medicinal/bioorganic chemistry and materials science.

1 Introduction

2 Methods for Incorporation/Manipulation of SF₄Cl/SF₅ Groups

2.1 Nonaromatic SF₅ Compounds via Direct Pentafluorosulfanylation of Alkenes and Alkynes

2.2 SF₄Cl- and SF₅-Aryl/Heteroaryl Derivatives

3 Synthesis of SF₅/SF₄Cl/SF₄-Substituted Small Molecules

3.1 Heterocycles

3.2 Amines and Amino Acids

3.3 α-SF₅ ketones

3.4 Miscellaneous Alkyl-, Alkenyl-, and Aryl-SF₅ Compounds

4 Medicinal/Biological Applications

4.1 Anticancer Compounds

4.2 Antibacterial and Antiparasitic Compounds

4.3 Central Nervous System

4.4 Miscellaneous Biological Activity

5 Materials Science Applications

6 Conclusion

Key words

pentafluorosulfanyl - chlorotetrafluorosulfanyl - synthesis - applications - materials Science - medicinal Chemistry - biological activity

Full Text

References

References
1 Chan JM. W. J. Mater. Chem. C 2019; 7: 12822

2a Haufe G. Tetrahedron 2022; 109: 132656 this Tetrahedron article appeared in the literature while this Short Review was being finalized.
2b Savoie PR, Welch JT. Chem. Rev. 2015; 115: 1130
2c Sowaileh MF, Hazlitt RA, Colby DA. ChemMedChem 2017; 12: 1481
2d Das P, Tokunaga E, Shibata N. Tetrahedron Lett. 2017; 58: 4803
2e Kanishchev OS, Dolbier WR. Jr. In Advances in Heterocyclic Chemistry, Vol. 120. Scriven E, Ramsden CA. Elsevier; Amsterdam: 2016: 1
2f Ponomarenko MV, Röschenthaler G.-V. In Frontiers of Organofluorine Chemistry . Ojima I. ??: 2020: 251

3 Dolbier WR, Aït-Mohand S, Schertz TD, Sergeeva TA, Cradlebaugh JA, Mitani A, Gard GL, Winter RW, Thrasher JS. J. Fluorine Chem. 2006; 127: 1302
4 Gilbert A, Paquin JF. J. Fluorine Chem. 2019; 221: 70
5 Gilbert A, Langowski P, Delgado M, Chabaud L, Pucheault M, Paquin JF. Beilstein J. Org. Chem. 2020; 16: 3069
6 Gilbert A, Birepinte M, Paquin JF. J. Fluorine Chem. 2021; 243: 109734

7a Birepinte M, Champagne PA, Paquin JF. Angew. Chem. Int. Ed. 2022; 61: e202112575
7b McTeague TA, Jamison FT. Angew. Chem. Int. Ed. 2016; 55: 15072

8a Rombach D, Wagenknecht HA. ChemCatChem 2018; 10: 2955
8b McTeague TA, Jamison FT. Angew. Chem. Int. Ed. 2016; 55: 15072

9 Rombach D, Wagenknecht HA. Angew. Chem. Int. Ed. 2020; 59: 300
10 Rombach D, Birenheide B, Wagenknecht HA. Chem. Eur. J. 2021; 27: 8088
11 Iakobson G, Pošta M, Beier P. J. Fluorine Chem. 2018; 213: 51
12 Umemoto T, Garrick LM, Saito N. Beilstein J. Org. Chem. 2012; 8: 461
13 Pitts CR, Bornemann D, Liebing P, Santschi N, Togni A. Angew. Chem. Int. Ed. 2019; 58: 1950
14 Saidalimu I, Liang Y, Niina K, Tanagawa K, Saito N, Shibata N. Org. Chem. Front. 2019; 6: 1157
15 Surjadinata G, Hunter L, Matesic L, Pascali G. J. Flow Chem. 2021; 11: 107
16 Wang L, Cornella J. Angew. Chem. Int. Ed. 2020; 59: 23510
17 Wang L, Ni S, Cornella J. Synthesis 2021; 53: 4308
18 Cui B, Jia S, Tokunaga E, Saito N, Shibata N. Chem. Commun. 2017; 53: 12738
19 Das P, Takada M, Matsuzaki K, Saito N, Shibata N. Chem. Commun. 2017; 53: 3850
20 Tanagawa K, Zhao Z, Saito N, Shibata N. Bull. Chem. Soc. Jpn. 2021; 94: 1682
21 Ajenjo J, Klepetářová B, Greenhall M, Bím D, Culka M, Rulíšek L, Beier P. Chem. Eur. J. 2019; 25: 11375
22 Pröhm P, Schmid JR, Sonnenberg K, Voßnacker P, Steinhauer S, Schattenberg CJ, Müller R, Kaupp M, Riedel S. Angew. Chem. Int. Ed. 2020; 59: 16002
23 Niina K, Tanagawa K, Sumii Y, Saito N, Shibata N. Org. Chem. Front. 2020; 7: 1276

24a Shou JY, Xu XH, Qing FL. Angew. Chem. Int. Ed. 2021; 60: 15271
24b Pitts CR, Santschi N, Togni A. WO 2019229103, 2019

25 Zhao Q, Vuong TM. H, Bai XF, Pannecoucke X, Xu LW, Bouillon JP, Jubault P. Chem. Eur. J. 2018; 24: 5644
26 Debrauwer V, Leito I, Lõkov M, Tshepelevitsh S, Parmentier M, Blanchard N, Bizet V. ACS Org. Inorg. Au 2021; 1: 43
27 Gilbert A, Bertrand X, Paquin JF. Org. Lett. 2018; 20: 7257
28 Roudias M, Gilbert A, Paquin JF. Eur. J. Org. Chem. 2019; 6655
29 Desroches J, Gilbert A, Houle C, Paquin JF. Synthesis 2017; 49: 4827
30 Grigolato L, Brittain WD. G, Hudson AS, Czyzewska MM, Cobb SL. J. Fluorine Chem. 2018; 212: 166
31 Hiscocks HG, Yit DL, Pascali G, Ung AT. Monatsh. Chem. 2021; 152: 449
32 Gilbert A, Langowski P, Paquin JF. Tetrahedron 2021; 98: 132424
33 Popov KK, Campbell JL. P, Kysilka O, Hošek J, Davies CD, Pour M, Kočovský P. J. Org. Chem. 2022; 87: 920

34a Dolbier WA. Jr, Aït-Mohand S, Schertz TD, Sergeeva TA, Cradlebaugh JA, Mitani A, Gard GL, Winter RW, Thrasher JS. A. J. Fluorine Chem. 2016; 127: 1302
34b Penger A, von Hahmann CN, Filatov AS, Welch JT. Beilstein J. Org. Chem. 2013; 9: 2675
34c Cloutier M, Roudias M, Paquin JF. Org. Lett. 2019; 21: 3866

35 Feng FF, Ma JA, Cahard D. J. Org. Chem. 2021; 86: 13808
36 Dreier AL, Matsnev AV, Thrasher JS, Haufe G. Beilstein J. Org. Chem. 2018; 14: 373
37 Dreier AL, Beutel B, Mück-Lichtenfeld C, Matsnev AV, Thrasher JS, Haufe G. J. Org. Chem. 2017; 82: 1638
38 Dudziński P, Husstedt WS, Matsnev AV, Thrasher JS, Haufe G. Org. Biomol. Chem. 2021; 19: 5607
39 Savoie PR, von Hahmann CN, Penger A, Wei Z, Welch JT. Org. Biomol. Chem. 2018; 16: 3151
40 Belina SP, Qing SY, Dudziński P, Matsnev AV, Mück-Lichtenfeld C, Haufe G, Thrasher JS. Helv. Chim. Acta 2021; 104: e2100138
41 Lefebvre G, Charron O, Cossy J, Meyer C. Org. Lett. 2021; 23: 5491
42 Le TV, Daugulis O. Chem. Commun. 2022; 58: 537
43 Jin J, Zhou Y, Yang D, Zhang Q, Wang MW, Lu W. Arch. Pharm. (Weinheim) 2018; 351: 1
44 Pertusati F, Ferla S, Bassetto M, Brancale A, Khandil S, Westwell AD, McGuigan C. Eur. J. Med. Chem. 2019; 180: 1
45 Das P, Tokunaga E, Akiyama H, Doi H, Saito N, Shibata N. Beilstein J. Org. Chem. 2018; 14: 364
46 Sansook S, Ocasio CA, Day IJ, Tizzard GJ, Coles SJ, Fedorov O, Bennett JM, Elkins JM, Spencer J. Org. Biomol. Chem. 2017; 15: 8655
47 Mori S, Tsuemoto N, Kasagawa T, Nakano E, Fujii S, Kagechika H. Chem. Pharm. Bull. 2019; 67: 1278
48 Schmitt F, Gold M, Begemann G, Andronache I, Biersack B, Schobert R. Bioorg. Med. Chem. 2017; 25: 4894
49 Al Nasr IS, Hanachi R, Said RB, Rahali S, Tangour B, Abdelwahab SI, Farasani A, Taha MM. E, Bidwai A, Koko WS, Khan TA, Schobert R, Biersack B. Bioorg. Chem. 2021; 114: 105099
50 Naclerio GA, Abutaleb NS, Onyedibe KI, Seleem MN, Sintim HO. RSC Med. Chem. 2020; 11: 102
51 Pujol E, Blanco-Cabra N, Julián E, Leiva R, Torrents E, Vázquez S. Molecules 2018; 23: e00615-21
52 Probst A, Pujol E, Häberli C, Keiser J, Vázquez S. Antimicrob. Agents Chemother. 2021; 65: e00615
53 Onyedibe KI, Dayal N, Sintim HO. RSC Med. Chem. 2021; 12: 1879
54 Moraski GC, Bristol R, Seeger N, Boshoff HI, Tsang PS. Y, Miller MJ. ChemMedChem 2017; 12: 1108
55 Elek M, Djokovic N, Frank A, Oljacic S, Zivkovic A, Nikolic K, Stark H. Arch. Pharm. (Weinheim) 2021; 354: e2000486
56 Jose A, Tareque RK, Mortensen M, Legay R, Coles SJ, Tizzard GJ, Greenland BW, Smart TG, Bagley MC, Spencer J. Tetrahedron 2021; 85: 132020
57 Zhang Y, Wang Y, He C, Liu X, Lu Y, Chen T, Pan Q, Xiong J, She M, Tu Z, Qin X, Li M, Tortorella MD, Talley J. J. Med. Chem. 2017; 60: 4135
58 Kim JG, Kang OY, Kim SM, Issabayeva G, Oh IS, Lee Y, Lee WH, Lim HJ, Park SJ. Molecules 2020; 25: 5536
59 Kandil S, Pannecouque C, Chapman FM, Westwell AD, McGuigan C. Bioorg. Med. Chem. Lett. 2019; 29: 126721
60 Qianzhu H, Welegedara AP, Williamson H, McGrath AE, Mahawaththa MC, Dixon NE, Otting G, Huber T. J. Am. Chem. Soc. 2020; 142: 17277
61 Shao P, Zhou Y, Yang D, Wang MW, Lu W, Jin J. Molecules 2019; 24: 4227
62 Sumii Y, Sasaki K, Tsuzuki S, Shibata N. Molecules 2019; 24: 3610
63 Liebing P, Pitts CR, Reimann M, Trapp N, Rombach D, Bornemann D, Kaupp M, Togni A. Chem. Eur. J. 2021; 27: 6086
64 Prinz C, Starke L, Ramspoth TF, Kerkering J, Martos Riaño V, Paul J, Neuenschwander M, Oder A, Radetzki S, Adelhoefer S, Ramos Delgado P, Aravina M, Millward JM, Fillmer A, Paul F, Siffrin V, von Kries JP, Niendorf T, Nazaré M, Waiczies S. ACS Sensors 2021; 6: 3948
65 Brel VK, Artyushin OI, Moiseeva AA, Sharova EV, Buyanovskaya AG, Nelyubina YV. J. Sulfur Chem. 2020; 41: 29
66 Gautam P, Wang Y, Zhang G, Sun H, Chan JM. W. Chem. Mater. 2018; 30: 7055
67 Ma XF, Luo XF, Yan ZP, Wu ZG, Zhao Y, Zheng YX, Zuo JL. Organometallics 2019; 38: 3553
68 Langford D, Göttker-Schnetmann I, Wimmer FP, Casper LA, Kenyon P, Winter RF, Mecking S. Organometallics 2019; 38: 2710
69 Kenyon P, Mecking S. J. Am. Chem. Soc. 2017; 139: 13786
70 Noonikara-Poyil A, Muñoz-Castro A, Boretskyi A, Mykhailiuk PK, Dias HV. R. Chem. Sci. 2021; 12: 14618
71 Qing SY, DeWeerd NJ, Matsnev AV, Strauss SH, Thrasher JS, Boltalina OV. J. Fluorine Chem. 2018; 211: 52