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-00000084.xml
Synthesis 2024; 56(15): 2379-2384
DOI: 10.1055/a-2290-6540
DOI: 10.1055/a-2290-6540
paper
Iodosulfonylation of [1.1.1]Propellane
This work was supported by the National Natural Science Foundation of China (22078300).
Abstract
An efficient disubstituted functionalization of [1.1.1]propellane has been developed. The protocol utilizes sulfonyl hydrazides and N-iodosuccinimide, enabling the introduction of iodine and sulfonyl groups into bicyclo[1.1.1]pentane (BCP) in moderate to excellent yields. It has the advantages of simple operation, mild conditions, and broad substrate scope.
Key words
[1.1.1]propellane - bicyclo[1.1.1]pentane - sulfonyl hydrazides - iodosulfonylation - radical reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2290-6540.
- Supporting Information
Publication History
Received: 19 December 2023
Accepted after revision: 19 March 2024
Accepted Manuscript online:
19 March 2024
Article published online:
08 April 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Gianatassio R, Lopchuk JM, Wang J, Pan C.-M, Malins LR, Prieto L, Brandt TA, Collins MR, Gallego GM, Sach NW, Spangler JE, Zhu H, Zhu J, Baran PS. Science 2016; 351: 241
- 2 Mykhailiuk PK. Org. Biomol. Chem. 2019; 17: 2839
- 3 Li Q, Li L, Xu Q.-L, Pan F. Org. Lett. 2022; 24: 4292
- 4 Goh YL, Cui YT, Pendharkar V, Adsool VA. ACS Med. Chem. Lett. 2017; 8: 516
- 5 Westphal MV, Wolfstädter BT, Plancher J.-M, Gatfield J, Carreira EM. ChemMedChem 2015; 10: 461
- 6 Makarov IS, Brocklehurst CE, Karaghiosoff K, Koch G, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 12774
- 7 Nugent J, Arroniz C, Shire BR, Sterling AJ, Pickford HD, Wong ML. J, Mansfield SJ, Caputo DF. J, Owen B, Mousseau JJ, Duarte F, Anderson EA. ACS Catal. 2019; 9: 9568
- 8 Kanazawa J, Uchiyama M. Synlett 2019; 30: 1
- 9 Ma X, Pham LN. Asian J. Org. Chem. 2020; 9: 8
- 10 He F.-S, Xie S, Yao Y, Wu J. Chin. Chem. Lett. 2020; 31: 3065
- 11 Yu Z, Shi L. Org. Chem. Front. 2022; 9: 3591
- 12 Shire BR, Anderson EA. JACS Au 2023; 3: 1539
- 13 Goeke A. Sulfur Rep. 2002; 23: 243
- 14 Reck F, Zhou F, Girardot M, Kern G, Eyermann CJ, Hales NJ, Ramsay RR, Gravestock MB. J. Med. Chem. 2005; 48: 499
- 15 Bunz U, Polborn K, Wagner H.-U, Szeimies G. Chem. Ber. 1988; 121: 1785
- 16 Bär RM, Kirschner S, Nieger M, Bräse S. Chem. Eur. J. 2018; 24: 1373
- 17 Bär RM, Gross PJ, Nieger M, Bräse S. Chem. Eur. J. 2020; 26: 4242
- 18a Wu Z, Xu Y, Liu J, Wu X, Zhu C. Sci. China: Chem. 2020; 63: 1025
- 18b Wu Z, Xu Y, Zhang H, Wu X, Zhu C. Chem. Commun. 2021; 57: 6066
- 19 Pickford HD, Ripenko V, McNamee RE, Holovchuk S, Thompson AL, Smith RC, Mykhailiuk PK, Anderson EA. Angew. Chem. Int. Ed. 2023; 62: e202213508
- 20 Yang F.-L, Tian S.-K. Tetrahedron Lett. 2017; 58: 487
- 21 Du B, Li Z, Qian P, Han J, Pan Y. Chem. Asian J. 2016; 11: 478
- 22 Tang S, Wu Y, Liao W, Bai R, Liu C, Lei A. Chem. Commun. 2014; 50: 4496
- 23 Chen R, Xu S, Shen F, Xu C, Wang K, Wang Z, Liu L. Molecules 2021; 26: 5551
- 24 Zhou C, Zeng X. Synthesis 2021; 53: 4614
- 25 Li X, Zhou C, Diao P, Ge Y, Guo C. Tetrahedron Lett. 2017; 58: 1296
- 26 Cao X, Cheng X, Xuan J. Org. Lett. 2018; 20: 449
- 27 Zhou G, Xu X.-D, Chen G.-P, Wei W.-T, Guo Z. Synlett 2018; 29: 2076