Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Mohamed Elsherbini; Arnaud Osi; Haifa Alharbi; Fatemah Karam; Thomas Wirth

doi:10.1055/a-1508-9593

Synthesis, Table of Contents

CC BY-NC-ND 4.0 · Synthesis 2023; 55(02): 307-314
DOI: 10.1055/a-1508-9593

paper

Special Issue dedicated to Prof. Alain Krief

Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Mohamed Elsherbini

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

^bNew address: Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK

,

Arnaud Osi

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

,

Haifa Alharbi

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

,

Fatemah Karam

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

,

Thomas Wirth ∗

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

› Author Affiliations

Abstract

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Dedicated to Prof. Alain Krief on the occasion of his 80^th birthday

Abstract

Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sulfur stereogenic centre are scarce and their synthesis is challenging. A small library of iodoarenes containing chiral sulfinamide and chiral sulfoximine moieties has been synthesised using commercially available reagents. The oxidation of the chiral iodoarene precursors to iodine(III) reagents was cumbersome due to facile overoxidation of the sulfoxide moiety and hence loss of chirality under various oxidation conditions. Oxidation of chiral sulfonimidoyl derivatives to the corresponding hypervalent iodine reagents was successful and led to novel sulfur-based chiral iodine(III) reagents.

Key words

hypervalent iodine - oxidation - stereoselective synthesis - sulfoximines - sulfur derivatives

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References

References
1 Parra A. Chem. Rev. 2019; 119: 12033
2 Ghosh S, Pradhan S, Chatterjee I. Beilstein J. Org. Chem. 2018; 14: 1244
3 Parra A, Reboredo S. Chem. Eur. J. 2013; 19: 17244
4 Kumar R, Wirth T. In Hypervalent Iodine Chemistry . Wirth T. Springer; Cham: 2016: 243
5 Ray DG. III, Koser GF. J. Am. Chem. Soc. 1990; 112: 5672
6 O’Mahony GE, Ford A, Maguire AR. J. Sulfur Chem. 2013; 34: 301
7 Quideau S, Pouységu L, Peixoto PA, Deffieux D. In Hypervalent Iodine Chemistry . Wirth T. Springer; Cham: 2016: 25
8 Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 9215
9 Dohi T, Sasa H, Miyazaki K, Fujitake M, Takenaga N, Kita Y. J. Org. Chem. 2017; 82: 11954
10 Hempel C, Maichle-Mössmer C, Pericàs MA, Nachtsheim BJ. Adv. Synth. Catal. 2017; 359: 2931
11 Hashimoto T, Shimazaki Y, Omatsu Y, Maruoka K. Angew. Chem. Int. Ed. 2018; 57: 7200
12 Hokamp T, Wirth T. Chem. Eur. J. 2020; 26: 10417
13 Mizar P, Wirth T. Angew. Chem. Int. Ed. 2014; 53: 5993
14 Wang Y, Yuan H, Lu H, Zheng WH. Org. Lett. 2018; 20: 2555
15 Abazid AH, Nachtsheim BJ. Angew. Chem. Int. Ed. 2020; 59: 1479
16 Lee JH, Choi S, Hong KB. Molecules 2019; 24: 2634
17 Li V, Chen P, Liu G. Beilstein J. Org. Chem. 2018; 14: 1813
18 Haubenreisser S, Wöste TH, Martínez C, Ishihara K, Muñiz K. Angew. Chem. Int. Ed. 2016; 55: 413
19 Banik SM, Medley JW, Jacobsen EN. J. Am. Chem. Soc. 2016; 138: 5000
20 Mizar P, Laverny A, El-Sherbini M, Farid U, Brown M, Malmedy F, Wirth T. Chem. Eur. J. 2014; 20: 9910
21 Maertens G, Canesi S. In Hypervalent Iodine Chemistry . Wirth T. Springer; Cham: 2016: 223
22 Qurban J, Elsherbini M, Wirth T. J. Org. Chem. 2017; 82: 11872
23 Ahmad A, Silva LF. J. Org. Chem. 2016; 81: 2174

24a Banik SM, Medley JW, Jacobsen EN. Science 2016; 353: 51
24b Sharma HA, Mennie KM, Kwan EE, Jacobsen EN. J. Am. Chem. Soc. 2020; 142: 16090

25 Hatzigrigoriou E, Varvoglis A, Bakola-Christianopoulou M. J. Org. Chem. 1990; 55: 315
26 Koposov AY, Boyarskikh VV, Zhdankin VV. Org. Lett. 2004; 6: 3613
27 Zhdankin VV, Smart JT, Zhao P, Kiprof P. Tetrahedron Lett. 2000; 41: 5299
28 Alharbi H, Elsherbini M, Qurban J, Wirth T. Chem. Eur. J. 2021; 27: 4317
29 Yang G.-H, Zheng H, Li X, Cheng J.-P. ACS Catal. 2020; 10: 2324
30 Kalim J, Duhail T, Le T.-N, Vanthuyne N, Anselmi E, Togni A, Magnier E. Chem. Sci. 2019; 10: 10516
31 Jaffe H, Leffler JE. J. Org. Chem. 1975; 40: 797
32 Rae J, Frey J, Jerhaoui S, Choppin S, Wencel-Delord J, Colobert F. ACS Catal. 2018; 8: 2805
33 Liu G, Cogan DA, Owens TD, Tang TP, Ellman JA. J. Org. Chem. 1999; 64: 1278
34 Fustero S, Ibáñez I, Barrio V, Maestro MA, Catalán S. Org. Lett. 2013; 15: 832
35 Elsherbini M, Wirth T. Tetrahedron 2018; 74: 3101
36 Colyer JT, Andersen NG, Tedrow JS, Soukup TS, Faul MM. J. Org. Chem. 2006; 71: 6859
37 Liu G, Cogan DA, Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913
38 CCDC-2074473 (6), CCDC-2074474 (8), CCDC-2074476 (9), and CCDC-2074475 (24) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
39 Elsherbini M, Wirth T. Chem. Eur. J. 2018; 24: 13399
40 Elsherbini M, Winterson B, Alharbi H, Folgueiras-Amador AA, Génot C, Wirth T. Angew. Chem. Int. Ed. 2019; 58: 9811
41 Yoshimura A, Klasen SC, Shea MT, Nguyen KC, Rohde GT, Saito A, Postnikov PS, Yusubov MS, Nemykin VN, Zhdankin VV. Chem. Eur. J. 2017; 23: 691
42 Koser GF, Wettach RH. J. Org. Chem. 1980; 45: 1542
43 Okamura H, Bolm C. Org. Lett. 2004; 6: 1305
44 Sen I, Sasmal S, Hall RG, Pal S. Synthesis 2016; 48: 3743
45 Maity A, Hyun S.-M, Powers DC. Nat. Chem. 2018; 10: 200
46 Qurban J, Elsherbini M, Alharbi H, Wirth T. Chem. Commun. 2019; 55: 7998
47 Nickerson LA, Bergstrom BD, Gao M, Shiue Y.-S, Laconsay CL, Cullberson MR, Knauss WA, Fettinger JC, Tantillo DJ, Shaw JT. Chem. Sci. 2020; 11: 494
48 Furukawa N, Akutagawa K, Yoshimura T, Oae S. Synthesis 1982; 77
49 Xie Y, Zhou B, Zhou S, Zhou S, Wei W, Liu J, Zhan Y, Cheng D, Chen M, Li Y. ChemistrySelect 2017; 2: 1620
50 Cheng Y, Dong W, Parthasarathy K, Bolm C. Org. Lett. 2017; 19: 726

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