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Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach

  • Ibuki Tanaka
    Ibuki Tanaka
    Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan
    More by Ibuki Tanaka
  • Masaya Sawamura*
    Masaya Sawamura
    Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan
    Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan
    *Email: [email protected]
  • , and 
  • Yohei Shimizu*
    Yohei Shimizu
    Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan
    Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan
    *Email: [email protected]
Cite this: Org. Lett. 2022, 24, 2, 520–524
Publication Date (Web):December 29, 2021
https://doi.org/10.1021/acs.orglett.1c03927
Copyright © 2021 American Chemical Society

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    Abstract

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    Reductive alkynylation of aldehydes by the Umpolung approach was developed using a photoredox catalyst under blue LED irradiation. Ketyl radicals, generated by single-electron reduction of aldehydes through proton-coupled electron transfer (PCET), reacted with electrophilic alkynylsulfones. Sterically demanding bulky aldehydes reacted smoothly under the Umpolung reaction conditions. Moreover, the alkynylation proceeded chemoselectively with an aryl aldehyde group in the presence of other carbonyl groups including an aliphatic aldehyde group.

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    Cited By

    This article is cited by 5 publications.

    1. Wenjuan Zhang, Juan Ren, Dawei Wang, Tian-Yu Sun, Xiao-Feng Xia. Selective Reduction of Triple Bond via Proton-Coupled Electron Transfer for the Synthesis of α,β-Unsaturated γ-Lactams. Organic Letters 2024, 26 (18) , 3982-3986. https://doi.org/10.1021/acs.orglett.4c01235
    2. Ravneet Kaur, Ravi P. Singh. Stereoselective Reductive Coupling Reactions Utilizing [1,2]-Phospha-Brook Rearrangement: A Powerful Umpolung Approach. The Journal of Organic Chemistry 2023, 88 (15) , 10325-10338. https://doi.org/10.1021/acs.joc.3c01055
    3. Jian Wang, Necip B. Üner, Scott Edwin Dubowsky, Matthew P. Confer, Rohit Bhargava, Yunyan Sun, Yuting Zhou, R. Mohan Sankaran, Jeffrey S. Moore. Plasma Electrochemistry for Carbon–Carbon Bond Formation via Pinacol Coupling. Journal of the American Chemical Society 2023, 145 (19) , 10470-10474. https://doi.org/10.1021/jacs.3c01779
    4. Qi Li, Wang Zhang, Chen Zhu, Hong Pan, Kang-Yue Shi, Yicheng Zhang, Man-Yi Han, Choon-Hong Tan. Organobase-Catalyzed Umpolung of Amides: The Generation and Transfer of Carbamoyl Anion. The Journal of Organic Chemistry 2023, 88 (2) , 1245-1255. https://doi.org/10.1021/acs.joc.2c02487
    5. Lailin Chen, Ya Li, Mingfeng Han, Yun Peng, Xiahe Chen, Siwei Xiang, Hong Gao, Tianhao Lu, Shu-Ping Luo, Bingwei Zhou, Huayue Wu, Yun-Fang Yang, Yunkui Liu. P/N-Heteroleptic Cu(I)-Photosensitizer-Catalyzed [3 + 2] Regiospecific Annulation of Aminocyclopropanes and Functionalized Alkynes. The Journal of Organic Chemistry 2022, 87 (22) , 15571-15581. https://doi.org/10.1021/acs.joc.2c02138

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