Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Xiao-Yue Chen; Yichen Wu; Peng Wang

doi:10.1055/s-0041-1737493

Synthesis, Table of Contents

Synthesis 2022; 54(18): 3928-3940
DOI: 10.1055/s-0041-1737493

short review

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Authors

Xiao-Yue Chen

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road, Shanghai 200032, P. R. of China
Yichen Wu

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road, Shanghai 200032, P. R. of China
Peng Wang ∗

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road, Shanghai 200032, P. R. of China

^bCAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road, Shanghai 200032, P. R. of China

^cSchool of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. of China

Abstract

All articles of this category

Abstract

Site-selective functionalization of simple arenes remains a paramount challenge due to the similarity of multiple C–H bonds in the same molecule with similar steric environment and electronic properties. Recently, the site-selective thianthrenation/phenoxathiination of arenes has become an attractive solution to reach this challenging goal and it has been applied in the late-stage functionalization of various bioactive molecules. This short review aims to summarize recent advances in the site-selective C–H functionalization of arenes via aryl thianthrenium salts, as well as mechanistic insights in the remarkable site-selectivity obtained in thianthrenation step.

1 Introduction

2 Site-Selective Thianthrenation of Arenes and Mechanistic Insight

3 Thianthrenation-Enabled Site-Selective Functionalization of Arenes

3.1 Thianthrenation-Enabled C(sp ²)–C Bond Formation Reaction

3.2 Thianthrenation-Enabled C(sp ²)–X Bond Formation Reaction

4 Conclusion and Outlook

Key words

thianthrenation - phenoxathiination - arene - sulfonium salts - C–H functionalization

Full Text

References

References

For selected reviews on non-directed C–H activation:

1a Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
1b Hartwig JF, Larsen MA. ACS Cent. Sci. 2016; 2: 281
1c Wedi P, van Gemmeren M. Angew. Chem. Int. Ed. 2018; 57: 13016
1d Dalton T, Faber T, Glorius F. ACS Cent. Sci. 2021; 7: 245

2a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
2b Campeau L.-C, Stuart DR, Fagnou K. Aldrichimica Acta 2007; 40: 35
2c Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
2d Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
2e McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
2f Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
2g Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
2h Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540
2i Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
2j Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
2k Hussain I, Singh T. Adv. Synth. Catal. 2014; 356: 1661
2l Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
2m Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787

For selected reviews on late-stage functionalization:

3a Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
3b Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW. Chem. Soc. Rev. 2016; 45: 546
3c Pouliot J.-R, Grenier F, Blaskovits JT, Beaupré S, Leclerc M. Chem. Rev. 2016; 116: 14225
3d Shugrue CR, Miller SJ. Chem. Rev. 2017; 117: 11894
3e Börgel J, Ritter T. Chem 2020; 6: 1877
3f Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primers 2021; 1: 43
3g Guillemard L, Kaplaneris N, Ackermann L, Johansson MJ. Nat. Rev. Chem. 2021; 5: 522

4a Taylor R. Electrophilic Aromatic Substitution . Wiley; New York: 1990
4b de la Mare PB. In Electrophilic Halogenation, Chapt. 5. Elmore DT, Leadbetter A, Schofield K. Cambridge University Press; Cambridge: 1976
4c Olah GA. Acc. Chem. Res. 1971; 4: 240

For selected reviews on directing group approaches for meta- and para-functionalization, see:

5a Yang J. Org. Biomol. Chem. 2015; 13: 1930
5b Li J, De Sarkar S, Ackermann L. Top. Organomet. Chem. 2016; 55: 217
5c Dey A, Sinha SK, Achar TK, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10820
5d Haldar C, Hoque ME, Bisht R, Chattopadhyay B. Tetrahedron Lett. 2018; 59: 1269

6a Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
6b Kuninobu Y, Torigoe T. Org. Biomol. Chem. 2020; 18: 4126
6c Haldar C, Hoque ME, Chaturvedi J, Hassan MM. M, Chattopadhyay B. Chem. Commun. 2021; 57: 13059
6d Cheng C, Hartwig JF. Science 2014; 343: 853
6e Saito Y, Segawa Y, Itami K. J. Am. Chem. Soc. 2015; 137: 5193
6f Haines BE, Saito Y, Segawa Y, Itami K, Musaev DG. ACS Catal. 2016; 6: 7536
6g Okumura S, Tang S, Saito T, Semba K, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2016; 138: 14699

7a Li H, Sun C.-L, Yu M, Yu D.-G, Li B.-J, Shi Z.-J. Chem. Eur. J. 2011; 17: 3593
7b Guo X, Li C.-J. Org. Lett. 2011; 13: 4977
7c Romero NA, Margrey KA, Tay NE, Nicewicz DA. Science 2015; 349: 1326
7d Boursalian GB, Ham WS, Mazzotti AR, Ritter T. Nat. Chem. 2016; 8: 810
7e Niu L, Yi H, Wang S, Liu T, Liu J, Lei A. Nat. Commun. 2017; 8: 14226
7f Yuan C, Zhu L, Zeng R, Lan Y, Zhao Y. Angew. Chem. Int. Ed. 2018; 57: 1277
7g Thakur A, Manisha, Kumar I, Sharma U. Asian J. Org. Chem. 2022; e202100804

For selected reviews on sulfonium salts:

8a Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
8b Kozhushkov SI, Alcarazo M. Eur. J. Inorg. Chem. 2020; 2486
8c Peter A, Perry GJ. P, Procter DJ. Adv. Synth. Catal. 2020; 362: 2135
8d Tian Z.-Y, Hu Y.-T, Teng H.-B, Zhang C.-P. Tetrahedron Lett. 2018; 59: 299
8e Nenaidenko VG, Balenkova ES. Russ. J. Org. Chem. 2003; 39: 291

For selected examples on other sulfonium salts mediated C–H functionalization:

9a Donck S, Baroudi A, Fensterbank L, Goddard J.-P, Ollivier C. Adv. Synth. Catal. 2013; 355: 1477
9b Minami H, Otsuka S, Nogi K, Yorimitsu H. ACS Catal. 2018; 8: 579
9c Aukland MH, Talbot FJ. T, Fernández-Salas JA, Ball M, Pulis AP, Procter DJ. Angew. Chem. Int. Ed. 2018; 57: 9785
9d Xu P, Zhao D, Berger F, Hamad A, Rickmeier J, Petzold R, Kondratiuk M, Bohdan K, Ritter T. Angew. Chem. Int. Ed. 2020; 59: 1956
9e Kafuta K, Korzun A, Böhm M, Golz C, Alcarazo M. Angew. Chem. Int. Ed. 2020; 59: 1950
9f Aukland MH, Šiaučiulis M, West A, Perry GJ. P, Procter DJ. Nat. Catal. 2020; 3: 163
9g Tian Z.-Y, Zhang C.-P. Org. Chem. Front. 2022; 9: 2220

10 Berger F, Plutschack MB, Riegger J, Yu W, Speicher S, Ho M, Frank N, Ritter T. Nature 2019; 567: 223

11a Wu J, Wang Z, Chen X.-Y, Wu Y, Wang D, Peng Q, Wang P. Sci. China Chem. 2020; 63: 336
11b Also see our preprint version on Chemrxiv: Wu J, Wang Z, Chen X.-Y, Wu Y, Wang D, Peng Q, Wang P. ChemRxiv 2019; preprint

12 Lucken EA. C. J. Chem. Soc. 1962; 4963
13 Shine HJ, Silber JJ. J. Org. Chem. 1971; 36: 2923
14 Kim K, Hull VJ, Shine HJ. J. Org. Chem. 1974; 39: 2534
15 Svanholm U, Hammerich O, Parker VD. J. Am. Chem. Soc. 1975; 97: 101
16 Svanholm U, Parker VD. J. Am. Chem. Soc. 1976; 98: 997
17 Tinker LA, Bard AJ. J. Electroanal. Chem. 1982; 133: 275
18 Chen J, Li J, Plutschack MB, Berger F, Ritter T. Angew. Chem. Int. Ed. 2020; 59: 5616
19 Juliá F, Shao Q, Duan M, Plutschack MB, Berger F, Mateos J, Lu C, Xue X.-S, Houk KN, Ritter T. J. Am. Chem. Soc. 2021; 143: 16041
20 Chen X.-Y, Nie X.-X, Wu Y, Wang P. Chem. Commun. 2020; 56: 5058
21 Tian Z.-Y, Lin Z.-H, Zhang C.-P. Org. Lett. 2021; 23: 4400
22 Alvarez EM, Karl T, Berger F, Torkowski L, Ritter T. Angew. Chem. Int. Ed. 2021; 60: 13609
23 Zhao Y, Yu C, Liang W, Patureau FW. Org. Lett. 2021; 23: 6232
24 Liang L, Niu H.-Y, Li R.-L, Wang Y.-F, Yan J.-K, Li C.-G, Guo H.-M. Org. Lett. 2020; 22: 6842
25 Lansbergen B, Granatino P, Ritter T. J. Am. Chem. Soc. 2021; 143: 7909
26 Nie X.-X, Huang Y.-H, Wang P. Org. Lett. 2020; 22: 7716
27 Zhang Y.-L, Wang G.-H, Wu Y, Zhu C.-Y, Wang P. Org. Lett. 2021; 23: 8522
28 Ye F, Berger F, Jia H, Ford J, Wortman A, Börgel J, Genicot C, Ritter T. Angew. Chem. Int. Ed. 2019; 58: 14615
29 Engl PS, Häring AP, Berger F, Berger G, Pérez-Bitrián A, Ritter T. J. Am. Chem. Soc. 2019; 141: 13346
30 Berger F, Alvarez EM, Frank N, Bohdan K, Kondratiuk M, Torkowski L, Engl PS, Barletta J, Ritter T. Org. Lett. 2020; 22: 5671
31 Sang R, Korkis SE, Su W, Ye F, Engl PS, Berger F, Ritter T. Angew. Chem. Int. Ed. 2019; 58: 16161
32 Zhao Y, Yu C, Liang W, Atodiresei IL, Patureau FW. Chem. Commun. 2022; 58: 284
33 Chen X.-Y, Huang Y.-H, Zhou J, Wang P. Chin. J. Chem. 2020; 38: 1269
34 Wu Y, Huang Y.-H, Chen X.-Y, Wang P. Org. Lett. 2020; 22: 6657
35 Selmani A, Gevondian AG, Schoenebeck F. Org. Lett. 2020; 22: 4802
36 Li J, Chen J, Sang R, Ham W.-S, Plutschack MB, Berger F, Chabbra S, Schnegg A, Genicot C, Ritter T. Nat. Chem. 2020; 12: 56
37 Alvarez EM, Plutschack MB, Berger F, Ritter T. Org. Lett. 2020; 22: 4593
38 Cabrera-Afonso MJ, Granados A, Molander GA. Angew. Chem. Int. Ed. 2022; 61: e202202706
39 Ye Y, Zhu J, Huang Y. Org. Lett. 2021; 23: 2386
40 Zhao D, Petzold R, Yan J, Muri D, Ritter T. Nature 2021; 600: 444