Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2024; 35(18): 2113-2116
DOI: 10.1055/s-0043-1763749
DOI: 10.1055/s-0043-1763749
letter
Expedient Synthesis of gem-CF2-2H-Thiophenes from Enaminothiones
The authors gratefully acknowledge funding from the National Natural Science Foundation of China (21971112 and 22361010).
Abstract
An expedient and easy-to-handle synthetic platform has been established for the constructing of 2H-thiophenes carrying fluorine atoms through [4+1] cyclization of enaminothiones with fluorinated carbene precursors. This simple reaction system is well compatible with a wide range of substrates under completely metal-free conditions. The resulting 2H-thiophenes can undergo further late-stage modifications to yield a wide range of fluorine-substituted heterocycles.
Key words
carbene chemistry - [4+1] cyclization - enaminothiones - fluorinated 2H-thiophenes - difluorocarbeneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763749.
- Supporting Information
- CIF File
Publication History
Received: 04 March 2024
Accepted after revision: 25 March 2024
Article published online:
08 April 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Xie Q, Hu J. Acc. Chem. Res. 2024; 57: 693
- 2 Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Acena JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
- 3 Meanwell NA. J. Med. Chem. 2018; 61: 5822
- 4 Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
- 5 Mendoza A, Bernardino SJ, Dweck MJ, Valencia I, Evans D, Tian H, Lee W, Li Y, Houk KN, Harran PG. J. Am. Chem. Soc. 2023; 145: 15888
- 6 Tsunemi T, Bernardino SJ, Mendoza A, Jones CG, Harran PG. Angew. Chem. Int. Ed. 2020; 59: 674
- 7 Abegg D, Tomanik M, Qiu N, Pechalrieu D, Shuster A, Commare B, Togni A, Herzon SB, Adibekian A. J. Am. Chem. Soc. 2021; 143: 20332
- 8 Muller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 9 Purser S, Moore P.-R, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 10 O’Hagan D. J. Fluorine Chem. 2010; 131: 1071
- 11 Zhang J, Xiong D, Jiang Z, Chen S, Huang GB, Li J, Wang Z, Yang J. Org. Lett. 2024; 26: 1447
- 12 Petrov VA, Marshall W. J. Fluor. Chem. 2015; 179: 56
- 13 Asr A, Emamian S, Aghaie M, Aghaie H. J. Fluor. Chem. 2018; 209: 14
- 14 Petrov V, Marchione AA, Dooley R. Chem. Commun. 2018; 54: 9298
- 15 Ying J, Liu T, Liu Y, Wan JP. Org. Lett. 2022; 24: 12 2404
- 16 Sheng H, Chen Z, Li X, Sua J, Song Q. Org. Chem. Front. 2022; 9: 3000
- 17 Mondal B, Nandi S, Pan SC. Eur. J. Org. Chem. 2017; 4666
- 18 Sato H, Yoshimura Y, Sakata S, Miura S, Machida H, Matsuda A. Bioorg. Med. Chem. Lett. 1998; 8: 989
- 19 Volkmann RA, Kelbaugh PR, Nason DM, Jasys VJ. J. Org. Chem. 1992; 57: 4352
- 20 Chen J, Guo P, Zhang J, Rong J, Sun W, Jiang Y, Loh TP. Angew. Chem. Int. Ed. 2019; 58: 12674
- 21 Liang X, Guo P, Yang W, Li M, Jiang C, Sun W, Loh TP, Jiang Y. Chem. Commun. 2020; 56: 2043
- 22 Rong J, Li H, Fu R, Sun W, Loh TP, Jiang Y. ACS Catal. 2020; 10: 3664
- 23 Wang F, Fu R, Chen J, Rong J, Wang E, Zhang J, Zhang Z, Jiang Y. Chem. Commun. 2022; 58: 3477
- 24 Li Y, Luo J, Jiang Y. Org. Chem. Front. 2023; 10: 5782
- 25 Zhang X, Zhang J, Chen J, Zhou B, Zhang J, Chen S, Jian W, Jiang Y. Org. Biomol. Chem. 2023; 21: 3345
- 26 Jiao Y, Wu T, Zhang X, Jiang Y. Org. Chem. Front. 2024; 11: 67
- 27 Palani V, Perea MA, Sarpong R. Chem. Rev. 2022; 122: 10126
- 28 Jia X, Li P, Shao Y, Yuan Y, Ji H, Hou W, Liu X, Zhang X. Green Chem. 2017; 19: 5568
- 29 Ho TL. Synth. Commun. 1979; 9: 37
- 30 Wang D, Kawahata M, Yang Z, Miyamoto K. Nat. Commun. 2016; 7: 12937
- 31 Guo L, Liu F, Wang L, Yuan H. Org. Chem. Front. 2020; 7: 1077