Synthesis
DOI: 10.1055/s-0042-1751535
paper
Special Issue New Trends in Organic Synthesis from Chinese Chemists

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

Xin Fang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
,
Xuebing Geng
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
,
Peng Wang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
b   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
,
Honghai Zhang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
c   State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
,
Saihu Liao  ∗
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
c   State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
› Author AffiliationsWe gratefully acknowledge the Recruitment Program of Global Experts, and the 100-talent project of Fujian, Fuzhou University, and Xiamen University for the financial support.
› Further Information
    Permissions and Reprints All articles of this category


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

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
    CrossrefPubMed
  • 2 Artschwager R, Ward DJ, Gannon S, Brouwer AJ, van de Langemheen H, Kowalski H, Liskamp RM. J. J. Med. Chem. 2018; 61: 5395
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 4 Hmissa T, Zhang X, Dhumal NR, McManus GJ, Zhou X, Nulwala HB, Mirjafari A. Angew. Chem. Int. Ed. 2018; 57: 16005
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 6 Liang D.-D, Streefkerk DE, Jordaan D, Wagemakers J, Baggerman J, Zuilhof H. Angew. Chem. Int. Ed. 2020; 59: 7494
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 8 Wei M, Liang D, Cao X, Luo W, Ma G, Liu Z, Li L. Angew. Chem. Int. Ed. 2021; 60: 7397
    CrossrefPubMed
  • 9 Lee C, Cook AJ, Elisabeth JE, Friede NC, Sammis GM, Ball ND. ACS Catal. 2021; 11: 6578
    CrossrefPubMed
  • 10 Dong J, Sharpless KB, Kwisnek L, Oakdale JS, Fokin VV. Angew. Chem. Int. Ed. 2014; 53: 9466
    CrossrefPubMed
  • 11 Durie K, Yatvin J, Kovaliov M, Crane GH, Horn J, Averick S, Locklin J. Macromolecules 2018; 51: 297
    Crossref
  • 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
    CrossrefPubMed
  • 13 Narayanan A, Jones LH. Chem. Sci. 2015; 6: 2650
    CrossrefPubMed
  • 14 Martín-Gago P, Olsen CA. Angew. Chem. Int. Ed. 2019; 58: 957
    CrossrefPubMed
  • 15 Dalton SE, Campos S. ChemBioChem 2020; 21: 1080
    CrossrefPubMed
  • 16 Jones LH, Kelly JW. RSC Med. Chem. 2020; 11: 10
    CrossrefPubMed
  • 17 Carneiro SN, Khasnavis SR, Lee J, Butler TW, Majmudar JD, am Ende CW, Ball ND. Org. Biomol. Chem. 2023; 21: 1356
    CrossrefPubMed
  • 18 Newhouse TR, Kaib PS. J, Gross AW, Corey EJ. Org. Lett. 2013; 15: 1591
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 20 Gao D.-W, Jamieson CS, Wang G, Yan Y, Zhou J, Houk KN, Tang Y. J. Am. Chem. Soc. 2021; 143: 80
    CrossrefPubMed
  • 21 Güttlein P, Schrey H, Zeng H, Schobert R. Org. Biomol. Chem. 2022; 20: 4794
    CrossrefPubMed
  • 22 Singh P, Mittal A, Bhardwaj A, Kaur S, Kumar S. Bioorg. Med. Chem. Lett. 2008; 18: 85
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 25 Erdem SS, Özpınar GA, Boz Ü. J. Enzyme. Inhib. Med. Chem. 2014; 29: 81
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 27 Wang P, Li S.-J, Zhang H, Yang N, Liao S. Synlett 2022; 34: 471
    Article in Thieme Connect
  • 28 Nie X, Xu T, Song J, Devaraj A, Zhang B, Chen Y, Liao S. Angew. Chem. Int. Ed. 2021; 133: 4002
    Crossref
  • 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
    CrossrefPubMed
  • 30 Dong X, Jiang W, Hua D, Wang X, Xu L, Wu X. Chem. Sci. 2021; 12: 11762
    CrossrefPubMed
  • 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
    PubMed
  • 32 Wang P, Zhang H, Nie X, Xu T, Liao S. Nat. Commun. 2022; 13: 3370
    CrossrefPubMed
  • 33 Cui J, Ke S, Zhao J, Wu S, Luo W, Xu S, Su X, Li Y. Org. Chem. Front. 2022; 9: 3540
    Crossref
  • 34 Frye NL, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2022; 61: e202115593
    CrossrefPubMed
  • 35 Zhang H, Yang N, Li J, Wang P, Li S, Xie L, Liao S. Org. Lett. 2022; 24: 8170
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 37 Erchinger JE, Hoogesteger R, Laskar R, Dutta S, Hümpel C, Rana D, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2023; 145: 2364
    CrossrefPubMed
  • 38 Yang N, Mao C, Zhang H, Wang P, Li S, Xie L, Liao S. Org. Lett. 2023; 25: 4478
    CrossrefPubMed
  • 39 Chan Y.-C, Wang X, Lam Y.-P, Wong J, Tse Y.-LS, Yeung Y.-Y. J. Am. Chem. Soc. 2021; 143: 12745
    PubMed
  • 40 Maji R, Ghosh S, Grossmann O, Zhang P, Leutzsch M, Tsuji N, List B. J. Am. Chem. Soc. 2023; 145: 8788
    CrossrefPubMed
  • 41 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462
    CrossrefPubMed
  • 42 Zhu R, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 12655
    CrossrefPubMed
  • 43 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 8069
    CrossrefPubMed
  • 44 Sha W, Zhang W, Ni S, Mei H, Han J, Pan Y. J. Org. Chem. 2017; 82: 9824
    CrossrefPubMed
  • 45 Zhang J, Zhou K, Wu J. Org. Chem. Front. 2018; 5: 813
    Crossref
  • 46 Ariyarathna JP, Wu F, Colombo SK, Hillary CM, Li W. Org. Lett. 2018; 20: 6462
    CrossrefPubMed
  • 47 Wang Y, Deng L, Zhou J, Wang X, Mei H, Han J, Pan Y. Adv. Synth. Catal. 2018; 360: 1060
    Crossref
  • 48 Xiong Y.-S, Zhang B, Yu Y, Weng J, Lu G. J. Org. Chem. 2019; 84: 13465
    CrossrefPubMed
  • 49 Yang Q, Lin Q.-Q, Xing H.-Y, Zhao Z.-G. Org. Chem. Front. 2019; 6: 3939
    Crossref
  • 50 Chan Y.-C, Wang X, Lam Y.-P, Wong J, Tse Y.-LS, Yeung Y.-Y. J. Am. Chem. Soc. 2021; 143: 12745
    CrossrefPubMed
  • 51 Li C, Qi Z.-C, Yang Q, Qiang X.-Y, Yang S.-D. Chin. J. Chem. 2018; 36: 1052
    Crossref
  • 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
    CrossrefPubMed
  • 53 Ma Q, Song J, Zhang X, Jiang Y, Ji L, Liao S. Nat. Commun. 2021; 12: 429
    CrossrefPubMed