Facile Synthesis of Diaryl Sulfones through Arylsulfonylation of Arynes and Thiosulfonates

Yating Zheng; Delin Tang; Pei Xie; Jinyun Luo; Zhihua Cai; Lin He

doi:10.1055/a-2004-1006

Synthesis, Table of Contents

Synthesis 2023; 55(08): 1253-1259
DOI: 10.1055/a-2004-1006

paper

Facile Synthesis of Diaryl Sulfones through Arylsulfonylation of Arynes and Thiosulfonates

Authors

Yating Zheng

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
Delin Tang

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
Pei Xie

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
Jinyun Luo

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
Zhihua Cai∗

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China
Lin He∗

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

^bKey Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. of China

Abstract

All articles of this category

Abstract

A mild and transition-metal-free arylsulfonylation reaction of arynes has been developed. Arynes generated in situ from 2-(trimethylsilyl)aryl triflates undergo nucleophilic addition with thiosulfonates to produce diaryl sulfones in 41–99% yield. The reaction can be scaled easily to gram-scale with the high yield maintained. Finally, mechanistic experiments showed that acetonitrile acted as a proton source.

Key words

arynes - thiosulfones - aryl sulfones - coupling - aryl–sulfur bonds

Full Text

References

References

1a Stearns BA, Baccei C, Bain G, Broadhead A, Clark RC, Coate H, Evans JF, Fagan P, Hutchinson JH, King C, Lee C, Lorrain DS, Prasit P, Prodanovich P, Santini A, Scott JM, Stock NS, Truong YP. Bioorg. Med. Chem. Lett. 2009; 19: 4647
1b Feng M, Tang B, Liang HS, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
1c Sulfur Chemistry. In Topics in Current Chemistry Collections . Jiang X. Springer; Cham: 2018
1d Yu G, Wang Q, Liu S, Zhang X, Che Q, Zhang G, Zhu T, Gu Q, Li D. J. Nat. Prod. 2019; 82: 998
1e Li P, Wang L, Wang X. J. Heterocycl. Chem. 2021; 58: 28

2a Crowley PJ, Fawcett J, Kariuki BM, Moralee AC, Percy JM, Salafia V. Org. Lett. 2002; 4: 4125
2b Blakemore PR. J. Chem. Soc, Perkin Trans. 1 2002; 23: 2563
2c Yang H, Carter RG, Zakharov LN. J. Am. Chem. Soc. 2008; 130: 9238
2d Söderman SC, Schwan AL. J. Org. Chem. 2012; 77: 10978
2e Wang Q.-G, Zhou Q.-Q, Deng J.-G, Chen Y.-C. Org. Lett. 2013; 15: 4786
2f Dussart N, Trinh HV, Gueyrard D. Org. Lett. 2016; 18: 4790
2g Trost BM, Kalnmals CA. Chem. Eur. J. 2019; 25: 11193
2h Oka N, Mori A, Suzuki K, Ando K. J. Org. Chem. 2021; 86: 657

3a Liu N.-W, Liang S, Manolikakes G. Synthesis 2016; 48: 1939
3b Shaaban S, Liang S, Liu N.-W, Manolikakes G. Org. Biomol. Chem. 2017; 15: 1947
3c Zhu J, Yang W.-C, Wang X.-D, Wu L. Adv. Synth. Catal. 2018; 360: 386
3d Joseph D, Idris MA, Chen J, Lee S. ACS Catal. 2021; 11: 4169
3e Liang S, Hofman K, Friedrich M, Keller J, Manolikakes G. ChemSusChem 2021; 14: 4878

4a Griffin RJ, Henderson A, Curtin NJ, Echalier A, Endicott JA, Hardcastle IR, Newell DR, Noble ME. M, Wang L.-Z, Golding BT. J. Am. Chem. Soc. 2006; 128: 6012
4b Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 3121
4c Cheng Z, Sun P, Tang A, Jin W, Liu C. Org. Lett. 2019; 21: 8925
4d Li X, Du J, Zhang Y, Chang H, Gao W, Wei W. Org. Biomol. Chem. 2019; 17: 3048
4e Xu X, Yan L, Wang S, Wang P, Yang A.-X, Li X, Lu H, Cao Z.-Y. Org. Biomol. Chem. 2021; 19: 8691

5a Olah GA, Kobayashi S, Nishimura J. J. Am. Chem. Soc. 1973; 95: 564
5b Ueda M, Uchiyama K, Kano T. Synthesis 1984; 323
5c Alizadeh A, Khodaei MM, Nazari E. Tetrahedron Lett. 2007; 48: 6805
5d Xu X.-H, Liu G.-K, Azuma A, Tokunaga E, Shibata N. Org. Lett. 2011; 13: 4854
5e Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
5f Pandya VG, Mhaske SB. Org. Lett. 2014; 16: 3836
5g Aithagani SK, Yempalla KR, Munagala G, Vishwakarma RA, Singh PP. RSC Adv. 2014; 4: 50208
5h Reddy RJ, Kumari AH. RSC Adv. 2021; 11: 9130
5i Hu Y, Huang Y, Zhao X, Gao Y, Li X, Chen Q. Org. Biomol. Chem. 2021; 19: 7066
5j Yoshii Y, Ito A, Hirashima T, Manabe O. Nippon Kagaku Kaishi 1986; 8: 1117

6a Nguyen B, Emmett EJ, Willis MC. J. Am. Chem. Soc. 2010; 132: 16372
6b Woolven H, González-Rodríguez C, Marco I, Thompson AL, Willis MC. Org. Lett. 2011; 13: 4876
6c Ye S, Wu J. Chem. Commun. 2012; 48: 10037
6d Deeming AS, Emmett EJ, Richards-Taylor CS, Willis MC. Synthesis 2014; 46: 2701
6e Liu G, Fan C, Wu J. Org. Biomol. Chem. 2015; 13: 1592
6f Ye S, Qiu G, Wu J. Chem. Commun. 2019; 55: 1013

7a Pandey AK, Kumar S, Singh R, Singh KN. Tetrahedron 2018; 74: 6704
7b Zhang Z, Wang S, Zhang Y, Zhang G. J. Org. Chem. 2019; 84: 3919
7c Gong X, Shen Z, Wang G, Qu L, Zhu C. Org. Biomol. Chem. 2021; 19: 10662
7d Wang X, Luo D, Wang X, Zeng X, Wang X, Hu Y. Tetrahedron Lett. 2021; 87: 153540

8a García-López J.-A, Greaney MF. Chem. Soc. Rev. 2016; 45: 6766
8b Bhojgude SS, Bhunia A, Biju AT. Acc. Chem. Res. 2016; 49: 1658
8c He J, Qiu D, Li Y. Acc. Chem. Res. 2020; 53: 508
8d Shi J, Li L, Li Y. Chem. Rev. 2021; 121: 3892

9a Ahire MM, Thoke MB, Mhaske SB. Org. Lett. 2018; 20: 848
9b Gakar RN, Bhattachariee S, Biju AT. Org. Lett. 2019; 21: 737
9c Saputra A, Fan R, Yao T, Chen J, Tan J. Adv. Synth. Catal. 2020; 362: 2683
9d Bhattacharjee S, Guin A, Gaykar RN, Biju AT. Org. Lett. 2020; 22: 9097
9e Gaykar RN, George M, Guin A, Bhattacharjee S, Biju AK. Org. Lett. 2021; 23: 3447
9f Zhao J, Larock RC. Org. Lett. 2005; 7: 4273
9g Zhao J, Larock RC. J. Org. Chem. 2007; 72: 583
9h Zhang L, Li X, Sun Y, Zhao W, Luo F, Huang X, Lin L, Yang Y, Peng B. Org. Biomol. Chem. 2017; 15: 7181
9i Li X, Sun Y, Huang X, Zhang L, Kong L, Peng B. Org. Lett. 2017; 19: 838
9j Shi J, Qiu D, Wang J, Xu H, Li Y. J. Am. Chem. Soc. 2015; 137: 5670
9k Garg P, Singh A. Org. Lett. 2018; 20: 1320
9l Cheng B, Li Y, Wang T, Zhang X, Li H, He Y, Li Y, Zhai H. J. Org. Chem. 2020; 85: 6794
9m Matsuzawa T, Hosoya T, Yoshida S. Chem. Sci. 2020; 11: 9691
9n Pawliczek M, Garve LK. B, Werz DB. Chem. Commun. 2015; 51: 9165
9o Zhao X, Huang Y, Qing F.-L, Xu X.-H. RSC Adv. 2017; 7: 47
9p Shigetomi T, Nojima A, Shioji K, Okuma K, Yokomori Y. Heterocycles 2006; 68: 2243
9q Huang Y, Chen Q. Chin. J. Org. Chem. 2020; 40: 4087
9r Matsuzawa T, Yoshida S, Hosoya T. Tetrahedron Lett. 2018; 59: 4197
9s Hazarika H, Gogoi P. Org. Biomol. Chem. 2021; 19: 8466

10a Hanamoto T, Korekoda K, Nakata K, Handa K, Koga Y, Kondo M. J. Fluorine Chem. 2002; 118: 99
10b Kopp F, Knochel P. Org. Lett. 2007; 9: 1639
10c Wunderlich SH, Knochel P. Angew. Chem. Int. Ed. 2007; 46: 7685
10d Saravanan P, Anbarasan P. Org. Lett. 2014; 16: 848
10e Yoshida S, Sugimura Y, Hazama Y, Nishiyama Y, Yano T, Shimizu S, Hosoya T. Chem. Commun. 2015; 51: 16613
10f Shyam PK, Jang H.-Y. J. Org. Chem. 2017; 82: 1761
10g Huang S, Thirupathi N, Tung C.-H, Xu Z. J. Org. Chem. 2018; 83: 9449
10h Song T, Li H, Wei F, Tung C.-H, Xu Z. Tetrahedron Lett. 2019; 60: 916
10i Wang W, Peng X, Wei F, Tung C.-H, Xu Z. Angew. Chem. Int. Ed. 2016; 55: 649
10j Huang S, Xia Z, Lu K, Lu H, Tung C.-H, Xu Z. Chin. J. Chem. 2020; 38: 1625
10k Qi J, Wei F, Huang S, Tung C.-H, Xu Z. Angew. Chem. Int. Ed. 2021; 60: 4561

11 Peng X, Ma C, Yung C.-H, Xu Z. Org. Lett. 2016; 18: 4154
12 Kanemoto K, Sakata Y, Hosoya T, Yoshida S. Chem. Lett. 2020; 49: 593

13a Cong Z.-S, Li Y.-G, Du G.-F, Gu C.-Z, Dai B, He L. Chem. Commun. 2017; 53: 13129
13b Lv Y.-F, Luo J.-Y, Ma Y.-C, Dong Q, He L. Org. Chem. Front. 2021; 8: 2461
13c Lv Y.-F, Luo J.-Y, Lin M.-Z, Yue H.-L, He L. Org. Chem. Front. 2021; 8: 5403
13d Lv Y.-F, Luo J.-Y, Lin M.-Z, He L, Yue H.-L, Liu R.-S, Wei W. Adv. Synth. Catal. 2021; 363: 5122
13e Luo J, Lin M, Wu L, Cai Z, He L, Du G. Org. Biomol. Chem. 2021; 19: 9237
13f Wang W, Wan H, Du G, Dai B, He L. Org. Lett. 2019; 21: 3496
13g Xie P, Yang S, Guo Y, Cai Z, Dai B, He L. J. Org. Chem. 2020; 85: 8872
13h An Y, Zhang F, Du G, Cai Z, He L. Org. Chem. Front. 2021; 8: 6979
13i Liu S, Xie P, Wu L, Zhao J, Cai Z, He L. Org. Chem. Front. 2022; 9: 1550

14a Kim D.-K, Um H.-S, Park H, Kim S, Lee C. Chem. Sci. 2020; 11: 13071
14b Lee HW, Lam FL, So CM, Lau CP, Chan AS. C, Kwong FY. Angew. Chem. Int. Ed. 2009; 48: 7436
14c Marquie J, Laporterie A, Dubac J. J. Org. Chem. 2001; 66: 421
14d Yang H, Li Y, Jiang M, Wang J, Fu H. Chem. Eur. J. 2011; 17: 5652
14e Liu X, Li W, Zheng D.-Q, Fan X.-N, Wu J. Tetrahedron 2015; 71: 3359
14f Zhu D.-L, Wu Q, Li H.-Y, Li H.-X, Lang J.-P. Chem. Eur. J. 2020; 26: 3484
14g Bahrami K, Khodei MM, Shahbazi F. Tetrahedron Lett. 2008; 49: 3931
14h Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2013; 52: 12679
14i Wu X.-M, Wang Y. Synlett 2014; 25: 1163

Supplementary Material

Supporting Information (PDF) (opens in new window)