Advances in the Synthesis of Sulfur-Containing Cyclic Architectures via Insertion of SO2

Xi Lu; Yuyang Huang; Yuxing Yang; Chao Shu

doi:10.1055/a-2301-2909

Synlett, Table of Contents

Synlett 2025; 36(01): 15-28
DOI: 10.1055/a-2301-2909

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Thieme Chemistry Journals Awardees 2024

Advances in the Synthesis of Sulfur-Containing Cyclic Architectures via Insertion of SO₂

Authors

Xi Lu
Yuyang Huang
Yuxing Yang
Chao Shu ∗

Abstract

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Abstract

Sulfur-containing heterocycles, where the S(R) moiety is located within the cyclic structure, have found tremendous applications in the fields of chemical, pharmaceutical, and materials sciences due to their unique chemical, biological and pharmaceutical activities. Recent years have witnessed increasing interest in sulfur-containing heterocycles, and new methods for their synthesis have been reported by adopting modern methodologies and technologies through insertion of sulfur dioxide. The main objective of this Account is to overview the latest major developments on the synthesis of sulfur-containing heterocyclic systems, mainly covering thermo-, photo- and electron-induced cyclization through the insertion of sulfur dioxide (SO₂). We aim to provide the readership with a comprehensive understanding of this topic and offer a positive outlook on the promising future of this field.

1 Introduction

2 Thermal-Induced Cyclization

3 Photoinduced Radical Cyclization

4 Electron-Induced Radical Cyclization

5 Conclusion

Key words

S-heterocycles - cyclization - sulfur dioxide - photocatalysis - electrocatalysis

Full Text

References

References

1a Feng M.-H, Tang B.-P, Liang HS, Jiang X.-F. Curr. Top. Med. Chem. 2016; 16: 1200
1b Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
1c Mondal S, Malakar S. Tetrahedron 2020; 76: 131662
1d Wang N, Saidhareddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246
1e Schank K. Synthesis of Open-Chain Sulfones . In The Chemistry of Sulphones and Sulphoxides . Patai S, Rappoport Z, Stirling C. John Wiley & Sons; New York: 1988
1f Yu J, Jiang X. Adv. Agrochem. 2023; 2: 3

2a Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
2b Jacks TE, Belmont DT, Briggs CA, Horne NM, Kanter GD, Karrick GL, Krikke JJ, McCabe RJ, Mustakis JG, Nanninga TN, Risedorph GS, Seamans RE, Skeean R, Winkle DD, Zennie TM. Org. Process Res. Dev. 2004; 8: 201
2c Debnath S, Mondal S. Eur. J. Org. Chem. 2018; 933

For selected reviews, see:

3a Dittmer DC, Hoey MD. Cyclic Sulphinic Acid Derivatives (Sultines and Sulphinamides). In The Chemistry of Sulphonic Acids, Esters and their Derivatives. Patai S, Rappoport Z. John Wiley & Sons; Chichester: 1990: 239
3b Bondarenko OB, Saginova LG, Zyk NV. Russ. Chem. Rev. 1996; 65: 147

For our group’s previous work on sultine chemistry, see:

4a Zhang Y, Li H, Yang X, Zhou P, Shu C. Chem. Commun. 2023; 59: 6272
4b Zhu Z, Deng Z, Ouyang X, Shu C. Synlett 2023; 34: 1943
4c Yang L, Li Y, Shu C. Acta Chim. Sin. 2024; 82: 171

For selected reviews, see:

5a Emmett EJ, Willis MC. Asian J. Org. Chem. 2015; 4: 602
5b Qiu G, Zhou K, Gao L, Wu J. Org. Chem. Front. 2018; 5: 691
5c Hofman K, Liu N.-W, Manolikakes G. Chem. Eur. J. 2018; 24: 11852
5d Ye S.-Q, Yang M, Wu J. Chem. Commun. 2020; 56: 4145

For selected recent examples, see:

6a He F.-S, Bao P, Yu F.-Y, Zeng L.-H, Deng W.-P, Wu J. Org. Lett. 2021; 23: 7472
6b Li Y.-P, Chen S.-H, Wang M, Jiang X.-F. Angew. Chem. Int. Ed. 2020; 59: 8907
6c Shan Q.-C, Liu S, Shen Y.-C, Ma M.-M, Duan X.-H, Gao P, Guo L.-N. Org. Lett. 2022; 24: 6653
6d Chen L, Zhou M, Shen L, He X.-C, Li X, Zhang X.-M, Lian Z. Org. Lett. 2021; 23: 4991

7 Luo Y, Pan X, Chen C, Lao L, Wu J. Chem. Commun. 2015; 51: 180
8 Mao R, Zheng D, Xia H, Wu J. Org. Chem. Front. 2016; 3: 693
9 Konishi H, Tanaka H, Manabe K. Org. Lett. 2017; 19: 1578
10 Wang M, Chen S, Jiang X. Org. Lett. 2017; 19: 4916
11 Meng Y, Wang M, Jiang X. Angew. Chem. Int. Ed. 2020; 59: 1346
12 Meng Y, Wang M, Jiang X. CCS Chem. 2021; 3: 17
13 Chen X, Tang B, He C, Ma J, Zhuang S, Wu Y, Wu A. Chem. Commun. 2020; 56: 13653
14 Chen X, Wang H, He C, Wu C, Tang B, Hu Y, He C, Ma J, Zhuang S, Yu Z, Wu Y, Wu A. Org. Lett. 2022; 24: 7659
15 Wu Y, Li C, Wei Z, Liao W. Org. Lett. 2022; 24: 9112
16 Wang L, Shen Y, Wang Y, Wang H, Hao W, Jiang B. Adv. Synth. Catal. 2023; 365: 1693
17 Hou X, Liu H, Huang H. Nat Commun. 2024; 12: 1480
18 Li Y, Mao R, Wu J. Org. Lett. 2017; 3: 4472
19 Li H, Zhang Y, Yang X, Deng Z, Zhu Z, Zhou P, Ouyang X, Yuan Y, Chen X, Yang L, Liu M, Shu C. Angew. Chem. Int. Ed. 2023; 135: e202300159
20 Zhang Y, Zhou P, Yang X, Li H, Deng Z, Ren M, Shu C. Adv. Synth. Catal. 2023; 365: 3478
21 Li H, Zhang Y, Zou X, Yang X, Zhou P, Ma X, Lu S, Sun Q, Shu C. ACS Catal. 2024; 14: 3664
22 Li Z, Jiao L, Sun Y, He Z, Wei Z, Liao W. Angew. Chem. Int. Ed. 2020; 59: 7266

23a Sun Y, Li C, Xi J, Wei Z, Liao W. Org. Chem. Front. 2023; 10: 705
23b Sun Y, Li C, Xi J, Wei Z, Liao W. Org. Chem. Front. 2023; 10: 1592