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Photoinduced Syntheses and Reactivities of Phosphorus-Containing Interelement Compounds

  • Yuki Yamamoto
    Yuki Yamamoto
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
  • Ryo Tanaka
    Ryo Tanaka
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
    More by Ryo Tanaka
  • Miyuto Ota
    Miyuto Ota
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
    More by Miyuto Ota
  • Misaki Nishimura
    Misaki Nishimura
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
  • Cong Chi Tran
    Cong Chi Tran
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
  • Shin-ichi Kawaguchi
    Shin-ichi Kawaguchi
    Center for Education and Research in Agricultural Innovation, Faculty of Agriculture, Saga University, 152-1 Shonan-cho Karatsu, Saga 847-0021, Japan
  • Shintaro Kodama
    Shintaro Kodama
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
  • Akihiro Nomoto
    Akihiro Nomoto
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
  • , and 
  • Akiya Ogawa*
    Akiya Ogawa
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan
    *E-mail: [email protected]
    More by Akiya Ogawa
Cite this: J. Org. Chem. 2020, 85, 22, 14708–14719
Publication Date (Web):October 28, 2020
https://doi.org/10.1021/acs.joc.0c02014
Copyright © 2020 American Chemical Society

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    Abstract

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    The photoinduced reactions of tetraphenyldiphosphine disulfide with a range of organic dichalcogenides successfully afforded a series of phosphorus(V)–chalcogen interelement compounds via a radical process. The relative reactivities of the organic dichalcogenides (i.e., (PhS)2, (PhSe)2, and (PhTe)2) toward the PIII or PV groups in the diphosphine analogues under light were investigated in detail, and a convenient method was developed to form P–S or P–Se interelement compounds from tetraphenyldiphosphine disulfide and (PhS)2 or (PhSe)2 upon photoirradiation. Furthermore, the relative photochemical properties and reactivities of tetraphenyldiphophine (P–P interelement compound) and its analogues toward photoinduced radical addition reactions were also discussed. The formed P–E (E = S, Se) interelement compounds could be utilized for ionic reactions, and they could be transformed into various phosphine reagents via one-pot processes.

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    • 1H NMR, 13C NMR, 31P NMR, and 77Se NMR spectra (PDF)

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    Cited By

    This article is cited by 8 publications.

    1. Yuki Yamamoto, Kohsuke Fujiwara, Akiya Ogawa. Palladium-Catalyzed Hydrophosphination of Terminal Alkynes with Diphenylphosphine Oxide in the Presence of Tetraphenyldiphosphine Monoxide. Organometallics 2023, 42 (18) , 2590-2597. https://doi.org/10.1021/acs.organomet.2c00659
    2. Yuki Yamamoto, Kohsuke Fujiwara, Ryo Tanaka, Hinako Watanabe, Akiya Ogawa. Iodine‐Catalyzed One‐pot Formation of Phosphorus‐Heteroatom Bonds from Stable Diphosphines in Air. Asian Journal of Organic Chemistry 2024, 13 (4) https://doi.org/10.1002/ajoc.202300654
    3. Yuki Yamamoto, Akiya Ogawa. Photoinduced Synthesis of Bisphosphinated Quinoxalines via Radical Cyclization of o ‐Diisocyanoarenes with Diphosphines. Chemistry – An Asian Journal 2023, 18 (8) https://doi.org/10.1002/asia.202201269
    4. Yuki Yamamoto, Akiya Ogawa. Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process. Molecules 2023, 28 (2) , 787. https://doi.org/10.3390/molecules28020787
    5. Leila Azad, Khadijeh Yadollahzadeh. Synthesis of new functionalized maleimides and phthalimides from maleimide, phthalimide, acetylenicesters, and phosphorus nucleophiles. Phosphorus, Sulfur, and Silicon and the Related Elements 2022, 197 (2) , 144-150. https://doi.org/10.1080/10426507.2021.2012678
    6. Yuki Yamamoto, Ryo Tanaka, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa. Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization. Molecules 2022, 27 (4) , 1284. https://doi.org/10.3390/molecules27041284
    7. Jairus L. Lamola, Joy C. Shilubana, Lonwabo Ngodwana, Banele Vatsha, Adedapo S. Adeyinka, Munaka C. Maumela, Cedric W. Holzapfel, Edwin M. Mmutlane. Easily Prepared Mono(N,N‐dialkylamino)phosphine Palladium(II) Complexes: Structural and Catalytic Evaluation. European Journal of Inorganic Chemistry 2021, 2021 (26) , 2578-2582. https://doi.org/10.1002/ejic.202100232
    8. Dat Phuc Tran, Yuki Sato, Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa. Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions. Beilstein Journal of Organic Chemistry 2021, 17 , 866-872. https://doi.org/10.3762/bjoc.17.72

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