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Palladium-Catalyzed Cascade Arylation of Vinylogous Esters Enabled by Tris(1-adamantyl)phosphine

  • Yi-Chi Yang
    Yi-Chi Yang
    Department of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan
    More by Yi-Chi Yang
  • Yi-Ching Lin
    Yi-Ching Lin
    Department of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan
    More by Yi-Ching Lin
  • , and 
  • Yen-Ku Wu*
    Yen-Ku Wu
    Department of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan
    *E-mail: [email protected]
    More by Yen-Ku Wu
Cite this: Org. Lett. 2019, 21, 23, 9286–9290
Publication Date (Web):October 8, 2019
https://doi.org/10.1021/acs.orglett.9b03071
Copyright © 2019 American Chemical Society

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    Abstract

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    Described is a method for the transformation of a cyclic vinylogous ester to the corresponding polyarylated product. We found a catalytic system comprising palladium diacetate and tris(1-adamantyl)phosphine is quite effective in promoting a set of controlled cascade arylations. As a result, a range of novel (hetero)aryl-containing scaffolds was synthesized with a high level of efficiency.

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    CCDC 19430731943074 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

    This article is cited by 9 publications.

    1. Guolin Xu, Peng Gao, Thomas J. Colacot. Tunable Unsymmetrical Ferrocene Ligands Bearing a Bulky Di-1-adamantylphosphino Motif for Many Kinds of Csp2–Csp3 Couplings. ACS Catalysis 2022, 12 (9) , 5123-5135. https://doi.org/10.1021/acscatal.2c00352
    2. Wei Wang, Jun Dai, Qiqiong Yang, Yu-Hua Deng, Fangzhi Peng, Zhihui Shao. Palladium-Catalyzed Asymmetric Direct Intermolecular Allylation of α-Aryl Cyclic Vinylogous Esters: Divergent Synthesis of (+)-Oxomaritidine and (−)-Mesembrine. Organic Letters 2021, 23 (3) , 920-924. https://doi.org/10.1021/acs.orglett.0c04125
    3. Wan-Ling Peng, Yin-Jia Jhang, Chieh-Yu Chang, Po-Kai Peng, Wei-Ting Zhao, Yen-Ku Wu. Total synthesis of (±)-mersicarpine following a 6- exo-trig radical cyclization. Organic & Biomolecular Chemistry 2022, 20 (31) , 6193-6195. https://doi.org/10.1039/D2OB00620K
    4. On Ying Yuen, Chau Ming So. Palladium-Catalyzed Site-Selective Arylation of α,β-Unsaturated Carbonyl Compounds through a Ligand-Controlled Strategy. Synlett 2022, 33 (09) , 805-814. https://doi.org/10.1055/s-0040-1719877
    5. Li-Dong Shao, Yang Chen, Mei Wang, Nan Xiao, Zhi-Jun Zhang, Dashan Li, Rong-Tao Li. Palladium-catalyzed direct γ-C(sp 3 )–H arylation of β-alkoxy cyclohexenones: reaction scope and mechanistic insights. Organic Chemistry Frontiers 2022, 9 (9) , 2308-2315. https://doi.org/10.1039/D1QO01871J
    6. Yi-Ching Lin, Ko-Wang Yen, Hsuan-Jen Lin, Yi-Chi Yang, Yen-Ku Wu. Haloarene-guided cascade arylation of cyclic vinylogous esters under palladium catalysis. Chemical Communications 2021, 57 (91) , 12119-12122. https://doi.org/10.1039/D1CC05006K
    7. Mei Wang, Wei Wang, Dashan Li, Wen-Jing Wang, Rui Zhan, Li-Dong Shao. α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds. Natural Products and Bioprospecting 2021, 11 (4) , 379-404. https://doi.org/10.1007/s13659-021-00312-1
    8. Yi‐Kang Song, Si‐Yu Xu, Shu‐Sheng Zhang, Jian‐Guo Fu, Guo‐Qiang Lin, Chen‐Guo Feng. Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2 H )‐Ones. Advanced Synthesis & Catalysis 2021, 363 (12) , 3001-3005. https://doi.org/10.1002/adsc.202001587
    9. Yu-Hsuan Chang, Wan-Ling Peng, I-Chia Chen, Hsin-Yun Hsu, Yen-Ku Wu. Palladium-catalyzed α-arylation of indolin-3-ones. Chemical Communications 2020, 56 (34) , 4660-4663. https://doi.org/10.1039/D0CC00435A

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