Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Yan-Ping Meng; Shi-Meng Wang; Wan-Yin Fang; Zhi-Zhong Xie; Jing Leng; Hamed Alsulami; Hua-Li Qin

doi:10.1055/s-0039-1690038

Synthesis, Table of Contents

Synthesis 2020; 52(05): 673-687
DOI: 10.1055/s-0039-1690038

short review

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Yan-Ping Meng

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

,

Shi-Meng Wang∗

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

^bSchool of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China

,

Wan-Yin Fang

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

^bSchool of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China

,

Zhi-Zhong Xie∗

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

,

Jing Leng

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

^bSchool of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China

,

Hamed Alsulami

^cDepartment of Mathematics, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia

,

Hua-Li Qin∗

^aSchool of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China Email: qinhuali@whut.edu.cn

^bSchool of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China

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Abstract

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Abstract

The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.

1 Introduction

2 Chemical Transformations of ESF

3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides

4 Novel SuFEx Reagents Derived from ESF

5 Applications of ESF Derivatives in Medicinal Chemistry

6 Applications of ESF Derivatives in Materials Science

7 Conclusion

Key words

sulfur(VI) fluoride exchange - ethenesulfonyl fluoride - 2-arylethenesulfonyl fluorides - sulfur(VI)-based molecules - medicinal chemistry - materials science

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References

References

1a Sharpless KB, Kolb HC. Book of Abstracts . 217th National Meeting of the American Chemical Society; Anaheim CA: Mar 21–25, 1999. American Chemical Society: Washington DC, 1999; ORGN-105, Accession Number 199:145537
1b Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004

2a Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
2b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596

3 Dong J, Krasnova L, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2014; 53: 9430

4a Dong J, Sharpless KB, Kwisnek L, Oakdale JS, Fokin VV. Angew. Chem. Int. Ed. 2014; 53: 9466
4b Li S, Wu P, Moses JE, Sharpless KB. Angew. Chem. Int. Ed. 2017; 56: 2903
4c 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
4d Liu Z, Li J, Li S, Li G, Sharpless KB, Wu P. J. Am. Chem. Soc. 2018; 140: 2919
4e Zheng Q, Woehl JL, Kitamura S, Santos-Martins D, Smedley CJ, Li G, Forli S, Moses JE, Wolan DW, Sharpless KB. Proc. Natl. Acad. Sci. U.S.A. 2019; 116: 18808
4f Barrow AS, Smedley CJ, Zheng Q, Li S, Dong J, Moses JE. Chem. Soc. Rev. 2019; 48: 4731

5a Meanwell NA. J. Med. Chem. 2011; 54: 2529
5b Drews J. Science 2000; 287: 1960
5c Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem. 2003; 10: 925
5d Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749

6a Rakesh KP, Wang S.-M, Leng J, Ravindar L, Asiri AM, Marwani HM, Qin H.-L. Anti-Cancer Agents Med. Chem. 2018; 18: 488
6b Zhao C, Rakesh KP, Ravidar L, Fang W, Qin H.-L. Eur. J. Med. Chem. 2019; 162: 679

7 Narayanan A, Jones LH. Chem. Sci. 2015; 6: 2650

8a Gold AM. Methods Enzymol. 1967; 11: 706
8b Fahrney D, Gold AM. J. Am. Chem. Soc. 1963; 85: 997

9 Zhao Q, Ouyang X, Wan X, Gajiwala KS, Kath JC, Jones LH, Burlingame AL, Taunton J. J. Am. Chem. Soc. 2017; 139: 680
10 Brouwer AJ, Álvarez NH, Ciaffoni A, van de Langemheen H, Liskamp RM. J. Bioorg. Med. Chem. 2016; 24: 3429

11a Nielsen MK, Ugaz CR, Li W, Doyle AG. J. Am. Chem. Soc. 2015; 137: 9571
11b Inkster JA. H, Liu K, Ait-Mohand S, Schaffer P, Guérin B, Ruth TJ, Storr T. Chem. Eur. J. 2012; 18: 11079
11c Yatvin J, Brooks K, Locklin J. Angew. Chem. Int. Ed. 2015; 54: 13370
11d Yatvin J, Brooks K, Locklin J. Chem. Eur. J. 2016; 22: 16348
11e Li S, Beringer LT, Chen S, Averick S. Polymer 2015; 78: 37

12 Hedrick RM. US Patent 2653973, 1953
13 Krutak JJ, Burpitt RD. US Patent 3952029, 1976
14 Fujigaya T, Sibasaki Y, Ando S, Kishimura S, Endo M, Sasago M, Ueda M. Chem. Mater. 2003; 15: 1512
15 Vries L. US Patent 4269790, 1981

16a Jimonet P, Audiau F, Barreau M, Blanchard J.-C, Boireau A, Bour Y, Coleno M.-A, Doble A, Doerflinger G, Do Huu C, Donat M.-H, Duchesne JM, Ganil P, Gueremy C, Honoré E, Just B, Kerphirique R, Gontier S, Hubert P, Laduron PM, Le Blevec J, Meunier M, Miquet J.-M, Nemecek C, Pasquet M, Piot O, Pratt J, Rataud J, Reibaud M, Stutzmann J.-M, Mignani S. J. Med. Chem. 1999; 42: 2828
16b Kreimeyer A, Laube B, Sturgess M, Goeldner M, Foucaud B. J. Med. Chem. 1999; 42: 4394
16c Aguilar B, Amissah F, Duverna R, Lamango NS. Curr. Cancer Drug Targets 2011; 11: 752

17 Krutak JJ, Burpitt RD, Moore WH, Hyatt JA. J. Org. Chem. 1979; 44: 3847
18 Zheng Q, Dong J, Sharpless KB. J. Org. Chem. 2016; 81: 11360
19 Chen Q, Mayer P, Mayr H. Angew. Chem. Int. Ed. 2016; 55: 12664
20 Daeniker H, Druey J. Helv. Chim. Acta 1962; 45: 1972
21 Chanet-Ray J, Vessiere R, Zéroual A. Heterocycles 1987; 26: 101
22 Mykhailiuk PK. Chem. Eur. J. 2014; 20: 4942
23 Slobodyanyuk EY, Artamonov OS, Shishkin OV, Mykhailiuk PK. Eur. J. Org. Chem. 2014; 2487
24 Mykhalchuk VL, Yarmolchuk VS, Doroschuk RO, Tolmachev AA, Grygorenko OO. Eur. J. Org. Chem. 2018; 2870
25 Jangra H, Chen Q, Fuks E, Zenz I, Mayer P, Ofial AR, Zipse H, Mayr H. J. Am. Chem. Soc. 2018; 140: 16758
26 Skalenko YA, Druzhenko TV, Denisenko AV, Samoilenko MV, Dacenko OP, Trofymchuk SA, Grygorenko OO, Tolmachev AA, Mykhailiuk PK. J. Org. Chem. 2018; 83: 6275
27 Qin H.-L, Zheng Q, Bare GA. L, Wu P, Sharpless KB. Angew. Chem. Int. Ed. 2016; 55: 14155
28 Chinthakindi PK, Govender KB, Kumar AS, Kruger HG, Govender T, Naicker T, Arvidsson PI. Org. Lett. 2017; 19: 480
29 Zha G.-F, Bare GA. L, Leng J, Shang Z.-P, Luo Z, Qin H.-L. Adv. Synth. Catal. 2017; 359: 3237
30 Zha G.-F, Zheng Q, Leng J, Wu P, Qin H.-L, Sharpless KB. Angew. Chem. Int. Ed. 2017; 56: 4849
31 Wang S.-M, Li C, Leng J, Bukhari SN. A, Qin H.-L. Org. Chem. Front. 2018; 5: 1411
32 Wang S.-M, Moku B, Leng J, Qin H.-L. Eur. J. Org. Chem. 2018; 4407
33 Li C, Wang S.-M, Qin H.-L. Org. Lett. 2018; 20: 4699
34 Ncube G, Huestis MP. Organometallics 2019; 38: 76
35 Li C, Qin H.-L. Org. Lett. 2019; 21: 4495
36 Liu M, Yang P, Karunananda MK, Wang Y, Liu P, Engle KM. J. Am. Chem. Soc. 2018; 140: 5805
37 Romine AM, Yang KS, Karunananda MK, Chen JS, Engle KM. ACS Catal. 2019; 9: 7626
38 Dou Y, Liu J, Jiang J, Zhu Q. Chem. Eur. J. 2019; 25: 6896
39 Park H, Li Y, Yu J.-Q. Angew. Chem. Int. Ed. 2019; 58: 11424
40 Chen X.-Y, Wu Y, Zhou J, Wang P, Yu J.-Q. Org. Lett. 2019; 21: 1426
41 Xu R, Xu T, Yang M, Cao T, Liao S. Nat. Commun. 2019; 10: 3752
42 Truce WE, Hoerger FD. J. Am. Chem. Soc. 1954; 76: 3230
43 Ungureanu A, Levens A, Candish L, Lupton DW. Angew. Chem. Int. Ed. 2015; 54: 11780
44 Chen X, Zha G.-F, Bare GA. L, Leng J, Wang S.-M, Qin H.-L. Adv. Synth. Catal. 2017; 359: 3254
45 Xu Y, Zhang Z, Jiang X, Chen X, Wang Z, Alsulami H, Qin H.-L, Tang W. Eur. J. Med. Chem. 2019; 181
46 Chen X, Zha G.-F, Fang W.-Y, Rakesh KP, Qin H.-L. Chem. Commun. 2018; 54: 9011
47 Khumalo MF, Akpan ED, Chinthakindi PK, Brasil EM, Rajbongshi KK, Makatini MM, Govender T, Kruger HG, Naicker T, Arvidsson PI. RSC Adv. 2018; 8: 37503
48 Arupula SK, Gudimella SK, Guin S, Mobin SM, Samanta S. Org. Biomol. Chem. 2019; 17: 3451
49 Li X.-R, Chen HJ, Wang W, Ma M, Chen Y, Li Y, Pullarkat SA, Leung P.-H. J. Organomet. Chem. 2019; 899
50 Liu H, Moku B, Li F, Ran J, Han J, Long S, Zha G.-F, Qin H.-L. Adv. Synth. Catal. 2019; 361: 4596
51 Moku B, Fang W.-Y, Leng J, Kantchev EA. B, Qin H.-L. ACS Catal. 2019; 9: 10477
52 Huang Y.-M, Wang S.-M, Leng J, Moku B, Zhao C, Alharbi NS, Qin H.-L. Eur. J. Org. Chem. 2019; 4597
53 Leng J, Qin H.-L. Chem. Commun. 2018; 54: 4477
54 Leng J, Alharbi NS, Qin H.-L. Eur. J. Org. Chem. 2019; 6101
55 Smedley CJ, Giel M.-C, Molino A, Barrow AS, Wilson DJ. D, Moses JE. Chem. Commun. 2018; 54: 6020
56 Thomas J, Fokin VV. Org. Lett. 2018; 20: 3749
57 Zhang X, Moku B, Leng J, Rakesh KP, Qin H.-L. Eur. J. Org. Chem. 2019; 1763
58 Shishido Y, Tomoike F, Kimura Y, Kuwata K, Yano T, Fukui K, Fujikawa H, Sekido Y, Murakami-Tonami Y, Kameda T, Shuto S, Abe H. Chem. Commun. 2017; 53: 11138
59 Zhang B, Pascali G, Wyatt N, Matesic L, Klenner MA, Sia TR, Guastella AJ, Massi M, Robinson AJ, Fraser BH. J. Labelled Compd. Radiopharm. 2018; 61: 847
60 Zhang B, Fraser BH, Klenner MA, Chen Z, Liang SH, Massi M, Robinson AJ, Pascali G. Chem. Eur. J. 2019; 25: 7613
61 Chen X, Zha G.-F, Wang JQ, Liu X.-H. J. Enzyme Inhib. Med. Chem. 2018; 33: 1266
62 Zha G.-F, Wang S.-M, Rakesh KP, Bukhari SN. A, Manukumar HM, Vivek HK, Mallesha N, Qin H.-L. Eur. J. Med. Chem. 2019; 162: 364
63 Jiang Y, Rakesh KP, Alharbi NS, Vivek HK, Manukumar HM, Mohammed YH. E, Qin H.-L. Bioorg. Chem. 2019; 89
64 Gao Y, Yan Z, Gray JL, He X, Wang D, Chen T, Huang Q, Li YC, Wang H, Kim SH, Mallouk TE, Wang D. Nat. Mater. 2019; 18: 384
65 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
66 Gahtory D, Sen R, Pujari S, Li S, Zheng Q, Moses JE, Sharpless KB, Zuilhof H. Chem. Eur. J. 2018; 24: 10550