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(11): 1727-1734
DOI: 10.1055/s-0042-1751535
DOI: 10.1055/s-0042-1751535
paper
New Trends in Organic Synthesis from Chinese Chemists
FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones
We gratefully acknowledge the Recruitment Program of Global Experts, and the 100-talent project of Fujian, Fuzhou University, and Xiamen University for the financial support.
Abstract
The incorporation of sulfonyl fluoride groups into molecules has been proven effective in enhancing their biological activities or introducing new functions. Herein, a transition-metal-free and visible-light-mediated radical tandem cyclization of unsaturated carboxylic acid is reported. This affords a facile access to FSO2-functionalized γ-lactones efficiently, which are critical structural motifs widely present in biologically active molecules.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751535.
- Supporting Information
Publication History
Received: 08 September 2023
Accepted after revision: 14 November 2023
Article published online:
19 December 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Liu Z, Li J, Li S, Li G, Sharpless KB, Wu P. J. Am. Chem. Soc. 2018; 140: 2919
- 2 Artschwager R, Ward DJ, Gannon S, Brouwer AJ, van de Langemheen H, Kowalski H, Liskamp RM. J. J. Med. Chem. 2018; 61: 5395
- 3 Kitamura S, Zheng Q, Woehl JL, Solania A, Chen E, Dillon N, Hull MV, Kotaniguchi M, Cappiello JR, Kitamura S, Nizet V, Sharpless KB, Wolan DW. J. Am. Chem. Soc. 2020; 142: 10899
- 4 Hmissa T, Zhang X, Dhumal NR, McManus GJ, Zhou X, Nulwala HB, Mirjafari A. Angew. Chem. Int. Ed. 2018; 57: 16005
- 5 Giel M.-C, Smedley CJ, Mackie ER. R, Guo T, Dong J, Soares da Costa TP, Moses JE. Angew. Chem. Int. Ed. 2020; 59: 1181
- 6 Liang D.-D, Streefkerk DE, Jordaan D, Wagemakers J, Baggerman J, Zuilhof H. Angew. Chem. Int. Ed. 2020; 59: 7494
- 7 Mahapatra S, Woroch CP, Butler TW, Carneiro SN, Kwan SC, Khasnavis SR, Gu J, Dutra JK, Vetelino BC, Bellenger J, am Ende CW, Ball ND. Org. Lett. 2020; 22: 4389
- 8 Wei M, Liang D, Cao X, Luo W, Ma G, Liu Z, Li L. Angew. Chem. Int. Ed. 2021; 60: 7397
- 9 Lee C, Cook AJ, Elisabeth JE, Friede NC, Sammis GM, Ball ND. ACS Catal. 2021; 11: 6578
- 10 Dong J, Sharpless KB, Kwisnek L, Oakdale JS, Fokin VV. Angew. Chem. Int. Ed. 2014; 53: 9466
- 11 Durie K, Yatvin J, Kovaliov M, Crane GH, Horn J, Averick S, Locklin J. Macromolecules 2018; 51: 297
- 12 Li S, Li G, Gao B, Pujari SP, Chen X, Kim H, Zhou F, Klivansky LM, Liu Y, Driss H, Liang D.-D, Lu J, Wu P, Zuilhof H, Moses J, Sharpless KB. Nat. Chem. 2021; 13: 858
- 13 Narayanan A, Jones LH. Chem. Sci. 2015; 6: 2650
- 14 Martín-Gago P, Olsen CA. Angew. Chem. Int. Ed. 2019; 58: 957
- 15 Dalton SE, Campos S. ChemBioChem 2020; 21: 1080
- 16 Jones LH, Kelly JW. RSC Med. Chem. 2020; 11: 10
- 17 Carneiro SN, Khasnavis SR, Lee J, Butler TW, Majmudar JD, am Ende CW, Ball ND. Org. Biomol. Chem. 2023; 21: 1356
- 18 Newhouse TR, Kaib PS. J, Gross AW, Corey EJ. Org. Lett. 2013; 15: 1591
- 19 Ogawa AK, Bunte EV, Mal R, Lan P, Sun Z, Crespo A, Wiltsie J, Clemas J, Gibson J, Contino L, Lisnock J, Zhou G, Garcia-Calvo M, Jochnowitz N, Ma X, Pan Y, Brown P, Zamlynny B, Bateman T, Leung D, Xu L, Tong X, Liu K, Crook M, Sinclair P. Bioorg. Med. Chem. Lett. 2016; 26: 2866
- 20 Gao D.-W, Jamieson CS, Wang G, Yan Y, Zhou J, Houk KN, Tang Y. J. Am. Chem. Soc. 2021; 143: 80
- 21 Güttlein P, Schrey H, Zeng H, Schobert R. Org. Biomol. Chem. 2022; 20: 4794
- 22 Singh P, Mittal A, Bhardwaj A, Kaur S, Kumar S. Bioorg. Med. Chem. Lett. 2008; 18: 85
- 23 Alapafuja SO, Nikas SP, Bharathan IT, Shukla VG, Nasr ML, Bowman AL, Zvonok N, Li J, Shi X, Engen JR, Makriyannis A. J. Med. Chem. 2012; 55: 10074
- 24 Brouwer AJ, Jonker A, Werkhoven P, Kuo E, Li N, Gallastegui N, Kemmink J, Florea BI, Groll M, Overkleeft HS, Liskamp RM. J. J. Med. Chem. 2012; 55: 10995
- 25 Erdem SS, Özpınar GA, Boz Ü. J. Enzyme. Inhib. Med. Chem. 2014; 29: 81
- 26 Cheng F, Wang L.-L, Mao Y.-H, Dong Y.-X, Liu B, Zhu G.-F, Yang Y.-Y, Guo B, Tang L, Zhang J.-Q. J. Org. Chem. 2021; 86: 8620
- 27 Wang P, Li S.-J, Zhang H, Yang N, Liao S. Synlett 2022; 34: 471
- 28 Nie X, Xu T, Song J, Devaraj A, Zhang B, Chen Y, Liao S. Angew. Chem. Int. Ed. 2021; 133: 4002
- 29 Chen D, Nie X, Feng Q, Zhang Y, Wang Y, Wang Q, Huang L, Huang S, Liao S. Angew. Chem. Int. Ed. 2021; 60: 27271
- 30 Dong X, Jiang W, Hua D, Wang X, Xu L, Wu X. Chem. Sci. 2021; 12: 11762
- 31 Wang P, Zhang H, Zhao M, Ji S, Lin L, Yang N, Nie X, Song J, Liao S. Angew. Chem. Int. Ed. 2022; 61: e2022076844
- 32 Wang P, Zhang H, Nie X, Xu T, Liao S. Nat. Commun. 2022; 13: 3370
- 33 Cui J, Ke S, Zhao J, Wu S, Luo W, Xu S, Su X, Li Y. Org. Chem. Front. 2022; 9: 3540
- 34 Frye NL, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2022; 61: e202115593
- 35 Zhang H, Yang N, Li J, Wang P, Li S, Xie L, Liao S. Org. Lett. 2022; 24: 8170
- 36 Zhang W, Li H, Li X, Zou Z, Huang M, Liu J, Wang X, Ni S, Pan Y, Wang Y. Nat. Commun. 2022; 13: 3515
- 37 Erchinger JE, Hoogesteger R, Laskar R, Dutta S, Hümpel C, Rana D, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2023; 145: 2364
- 38 Yang N, Mao C, Zhang H, Wang P, Li S, Xie L, Liao S. Org. Lett. 2023; 25: 4478
- 39 Chan Y.-C, Wang X, Lam Y.-P, Wong J, Tse Y.-LS, Yeung Y.-Y. J. Am. Chem. Soc. 2021; 143: 12745
- 40 Maji R, Ghosh S, Grossmann O, Zhang P, Leutzsch M, Tsuji N, List B. J. Am. Chem. Soc. 2023; 145: 8788
- 41 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462
- 42 Zhu R, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 12655
- 43 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 8069
- 44 Sha W, Zhang W, Ni S, Mei H, Han J, Pan Y. J. Org. Chem. 2017; 82: 9824
- 45 Zhang J, Zhou K, Wu J. Org. Chem. Front. 2018; 5: 813
- 46 Ariyarathna JP, Wu F, Colombo SK, Hillary CM, Li W. Org. Lett. 2018; 20: 6462
- 47 Wang Y, Deng L, Zhou J, Wang X, Mei H, Han J, Pan Y. Adv. Synth. Catal. 2018; 360: 1060
- 48 Xiong Y.-S, Zhang B, Yu Y, Weng J, Lu G. J. Org. Chem. 2019; 84: 13465
- 49 Yang Q, Lin Q.-Q, Xing H.-Y, Zhao Z.-G. Org. Chem. Front. 2019; 6: 3939
- 50 Chan Y.-C, Wang X, Lam Y.-P, Wong J, Tse Y.-LS, Yeung Y.-Y. J. Am. Chem. Soc. 2021; 143: 12745
- 51 Li C, Qi Z.-C, Yang Q, Qiang X.-Y, Yang S.-D. Chin. J. Chem. 2018; 36: 1052
- 52 Rao W.-H, Li Q, Chen F.-Y, Jiang L.-L, Xu P, Deng X.-W, Li M, Zou G.-D, Cao X. J. Org. Chem. 2021; 86: 11998
- 53 Ma Q, Song J, Zhang X, Jiang Y, Ji L, Liao S. Nat. Commun. 2021; 12: 429