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

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

› Author Affiliations

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