IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-33821-9.html
   My bibliography  Save this article

Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations

Author

Listed:
  • Zhenghui Wen

    (University of Amsterdam)

  • Diego Pintossi

    (University of Amsterdam)

  • Manuel Nuño

    (Fornham St Genevieve, Bury St Edmunds)

  • Timothy Noël

    (University of Amsterdam)

Abstract

Photocatalytic hydrogen atom transfer (HAT) processes have been the object of numerous studies showcasing the potential of the homogeneous photocatalyst tetrabutylammonium decatungstate (TBADT) for the functionalization of C(sp3)–H bonds. However, to translate these studies into large-scale industrial processes, careful considerations of catalyst loading, cost, and removal are required. This work presents organic solvent nanofiltration (OSN) as an answer to reduce TBADT consumption, increase its turnover number and lower its concentration in the product solution, thus enabling large-scale photocatalytic HAT-based transformations. The operating parameters for a suitable membrane for TBADT recovery in acetonitrile were optimized. Continuous photocatalytic C(sp3)-H alkylation and amination reactions were carried out with in-line TBADT recovery via two OSN steps. Promisingly, the observed product yields for the reactions with in-line catalyst recycling are comparable to those of reactions performed with pristine TBADT, therefore highlighting that not only catalyst recovery (>99%, TON > 8400) is a possibility, but also that it does not happen at the expense of reaction performance.

Suggested Citation

  • Zhenghui Wen & Diego Pintossi & Manuel Nuño & Timothy Noël, 2022. "Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33821-9
    DOI: 10.1038/s41467-022-33821-9
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-33821-9
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-022-33821-9?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    1. John J. Murphy & David Bastida & Suva Paria & Maurizio Fagnoni & Paolo Melchiorre, 2016. "Asymmetric catalytic formation of quaternary carbons by iminium ion trapping of radicals," Nature, Nature, vol. 532(7598), pages 218-222, April.
    2. Ian B. Perry & Thomas F. Brewer & Patrick J. Sarver & Danielle M. Schultz & Daniel A. DiRocco & David W. C. MacMillan, 2018. "Direct arylation of strong aliphatic C–H bonds," Nature, Nature, vol. 560(7716), pages 70-75, August.
    Full references (including those not matched with items on IDEAS)

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Yingguo Li & Jialun He & Guilong Lu & Chensheng Wang & Mengmeng Fu & Juan Deng & Fu Yang & Danfeng Jiang & Xiao Chen & Ziyi Yu & Yan Liu & Chao Yu & Yong Cui, 2024. "De novo construction of amine-functionalized metal-organic cages as heterogenous catalysts for microflow catalysis," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Hao Yang & Jinhui Xu & Hui Cao & Jie Wu & Dan Zhao, 2023. "Recovery of homogeneous photocatalysts by covalent organic framework membranes," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Yujun Li & Shaopeng Guo & Qing-Han Li & Ke Zheng, 2023. "Metal-free photoinduced C(sp3)–H/C(sp3)–H cross-coupling to access α‑tertiary amino acid derivatives," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    2. Ping-Fu Zhong & Jia-Lin Tu & Yating Zhao & Nan Zhong & Chao Yang & Lin Guo & Wujiong Xia, 2023. "Photoelectrochemical oxidative C(sp3)−H borylation of unactivated hydrocarbons," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    3. Long Huang & Marcin Szewczyk & Rajesh Kancherla & Bholanath Maity & Chen Zhu & Luigi Cavallo & Magnus Rueping, 2023. "Modulating stereoselectivity in allylic C(sp3)-H bond arylations via nickel and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    4. Geun Seok Lee & Beomsoon Park & Soon Hyeok Hong, 2022. "Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    5. Yue Wang & Suping Zhang & Ke Zeng & Pengli Zhang & Xiaorong Song & Tie-Gen Chen & Guoqin Xia, 2024. "Deoxygenative radical cross-coupling of C(sp3)−O/C(sp3)−H bonds promoted by hydrogen-bond interaction," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33821-9. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.