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Synthesis
DOI: 10.1055/a-2020-8828
paper
Special Issue New Trends in Organic Synthesis from Chinese Chemists

Synthesis of 1-Thiaphenalene Derivatives via Radical Cyclization of 1-Naphthalenesulfonyl Chlorides with Alkynes

Youhao Wei‡
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
,
Jige Liu‡
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
,
Xinxin Wu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
,
Yasu Chen
b   Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China
,
Chen Zhu  ∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
b   Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China
› Author AffiliationsWe are grateful for financial support from the National Natural Science Foundation of China (21971173, 22001185, and 22171201), the Natural Science Foundation of Jiangsu Province (BK20200852), the Natural Science Fund for Colleges and Universities in Jiangsu Province (20KJB150010), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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Dedicated to Professor Shigeru Yamago on the occasion of his 60th birthday

Abstract

Functionalized thiaphenalene derivatives are of high synthetic value, yet their preparation remains underexplored. Herein, we report an efficient approach for the synthesis of 1-thiaphenalene derivatives through radical cyclization of 1-naphthalenesulfonyl chlorides with alkynes. A variety of 1-thiaphenalene derivatives are readily furnished that are otherwise difficult to prepare by present methods. The protocol features mild photocatalytic conditions, broad functional-group compatibility, and high product diversity.

Key words

radical reactions - sulfonyl chloride - cyclization - photocatalysis - alkynes - thiaphenalene

Supporting Information



Publication History

Received: 20 December 2022

Accepted after revision: 26 January 2023

Accepted Manuscript online:
26 January 2023

Article published online:
02 March 2023

© 2023. Thieme. All rights reserved

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  • References

    • 1a Castán JM. A, Dalinot C, Dayneko S, Galan LA, Marqués PS, Alévêque O, Allain M, Maury O, Favereau L, Blanchard P, Welch GC, Cabanetos C. Chem. Commun. 2020; 56: 10131
      CrossrefPubMed
    • 1b Galán LA, Castán JM. A, Dalinot C, Marqués PS, Blanchard P, Maury O, Cabanetos C, Bahers TL, Monnereau C. Phys. Chem. Chem. Phys. 2020; 22: 12373
      CrossrefPubMed
    • 1c Zhang S, Chen Y, Liu Z, Fang Q. J. Photochem. Photobiol., A 2015; 311: 25
      Crossref
  • 2 Si E, Zhao P, Wang L, Duan Z, Mathey F. Eur. J. Org. Chem. 2020; 697
    CrossrefPubMed
    • 3a Muriel B, Waser J. Angew. Chem. Int. Ed. 2021; 60: 4075
      CrossrefPubMed
    • 3b Yao Q, Kong L, Wang M, Yuan Y, Sun R, Li Y. Org. Lett. 2018; 20: 1744
      CrossrefPubMed
    • 3c Yu Q, Zhang J, Wu F, Liu X, Wang C, Zhang J, Rong L. J. Org. Chem. 2022; 87: 7136
      CrossrefPubMed
    • 3d Trogolo D, Maranzana A, Ghigo G, Tonachini G. Combust. Flame 2016; 168: 331
      Crossref
  • 4 Zeng X, Ilies L, Nakamura E. Org. Lett. 2012; 14: 954
    CrossrefPubMed
  • 5 Domínguez AG, Müller S, Nevado C. Angew. Chem. Int. Ed. 2017; 56: 9949
    CrossrefPubMed
    • 6a Liu Y, Song R, Li J. Sci. China Chem. 2016; 59: 161
      Crossref
    • 6b Sicignano M, Rodríguez RI, Alemán J. Eur. J. Org. Chem. 2021; 3303
      CrossrefPubMed
  • 7 CCDC 2214299 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
    • 8a Dixon IM, Collin JP, Sauvage JP, Flamigni L, Encinasb S, Barigelletti F. Chem. Soc. Rev. 2000; 29: 385
      Crossref
    • 8b Zhang P, Shi S, Gao X, Han S, Lin J, Zhao Y. Org. Biomol. Chem. 2019; 17: 2873
      CrossrefPubMed
  • 9 Verhaegen Y, Liu L, Nguyen TT, Loy TV, Voet AR. D, Schols D, Dehaen W, Jonghe SD. Bioorg. Chem. 2021; 107: 104560
    CrossrefPubMed