FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones

Xin Fang; Xuebing Geng; Peng Wang; Honghai Zhang; Saihu Liao

doi:10.1055/s-0042-1751535

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(11): 1727-1734
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

Autoren

Xin Fang

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
Xuebing Geng

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
Peng Wang

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China

^bKey Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
Honghai Zhang

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China

^cState Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
Saihu Liao ∗

^aKey Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China

^cState Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China

Abstract

Alle Artikel dieser Rubrik

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.

Key words

FSO₂ radical - photoredox - γ-lactone - cyclization - difunctionlization

Volltext

Referenzen

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

Zusatzmaterial

Supporting Information (PDF) (opens in new window)