IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-29984-0.html
   My bibliography  Save this article

Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C–C bond-functionalization

Author

Listed:
  • Xin-Yang Lv

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16
    Universitat Rovira i Virgili, c/Marcel·lí Domingo, 1)

  • Roman Abrams

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16)

  • Ruben Martin

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16
    Universitat Rovira i Virgili, c/Marcel·lí Domingo, 1
    ICREA, Passeig Lluís Companys, 23)

Abstract

C–C bond forming cross-couplings are convenient technologies for the construction of functional molecules. Consequently, there is continual interest in approaches that can render traditionally inert functionality as cross-coupling partners, included in this are ketones which are widely-available commodity chemicals and easy to install synthetic handles. Herein, we describe a dual catalytic strategy that utilizes dihydroquinazolinones derived from ketone congeners as adaptative one-electron handles for forging C(sp3) architectures via α C–C cleavage with aryl and alkyl bromides. Our approach is achieved by combining the flexibility and modularity of nickel catalysis with the propensity of photoredox events for generating open-shell reaction intermediates. This method is distinguished by its wide scope and broad application profile––including chemical diversification of advanced intermediates––, providing a catalytic technique complementary to existing C(sp3) cross-coupling reactions that operates within the C–C bond-functionalization arena.

Suggested Citation

  • Xin-Yang Lv & Roman Abrams & Ruben Martin, 2022. "Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C–C bond-functionalization," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29984-0
    DOI: 10.1038/s41467-022-29984-0
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-29984-0
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-29984-0?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. Sarah Z. Tasker & Eric A. Standley & Timothy F. Jamison, 2014. "Recent advances in homogeneous nickel catalysis," Nature, Nature, vol. 509(7500), pages 299-309, May.
    2. Sarah Z. Tasker & Eric A. Standley & Timothy F. Jamison, 2014. "Erratum: Recent advances in homogeneous nickel catalysis," Nature, Nature, vol. 510(7503), pages 176-176, June.
    Full references (including those not matched with items on IDEAS)

    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. Liuzhuang Xing & Qian Yang & Chen Zhu & Yilian Bai & Yurong Tang & Magnus Rueping & Yunfei Cai, 2023. "Poly(heptazine imide) ligand exchange enables remarkable low catalyst loadings in heterogeneous metallaphotocatalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    2. Yuxi Gao & Lijuan Gao & Endiao Zhu & Yunhong Yang & Mi Jie & Jiaqian Zhang & Zhiqiang Pan & Chengfeng Xia, 2023. "Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    3. Xiao-Xu Wang & Yuan-Tai Xu & Zhi-Lin Zhang & Xi Lu & Yao Fu, 2022. "NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes and the ligand effects on regioselectivity," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    4. Xu Luo & Dali Yang & Xiaoqian He & Shengchun Wang & Dongchao Zhang & Jiaxin Xu & Chih-Wen Pao & Jeng-Lung Chen & Jyh-Fu Lee & Hengjiang Cong & Yu Lan & Hesham Alhumade & Janine Cossy & Ruopeng Bai & Y, 2023. "Valve turning towards on-cycle in cobalt-catalyzed Negishi-type cross-coupling," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    5. Wenfeng Liu & Yunxin Xing & Denghong Yan & Wangqing Kong & Kun Shen, 2024. "Nickel-catalyzed electrophiles-controlled enantioselective reductive arylative cyclization and enantiospecific reductive alkylative cyclization of 1,6-enynes," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
    6. Xi-Chao Wang & Bo Li & Cheng-Wei Ju & Dongbing Zhao, 2022. "Nickel(0)-catalyzed divergent reactions of silacyclobutanes with internal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    7. Yuli He & Jiawei Ma & Huayue Song & Yao Zhang & Yong Liang & You Wang & Shaolin Zhu, 2022. "Regio- and enantioselective remote hydroarylation using a ligand-relay strategy," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    8. Fang Zhu & Chao-Xing Li & Zhu-Lian Wu & Tian Cai & Wei Wen & Qi-Xiang Guo, 2022. "Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    9. Wenfeng Liu & Wei Li & Weipeng Xu & Minyan Wang & Wangqing Kong, 2024. "Nickel-catalyzed switchable arylative/endo-cyclization of 1,6-enynes," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    10. Stefano Bonciolini & Antonio Pulcinella & Matteo Leone & Debora Schiroli & Adrián Luguera Ruiz & Andrea Sorato & Maryne A. J. Dubois & Ranganath Gopalakrishnan & Geraldine Masson & Nicola Ca’ & Stefan, 2024. "Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    11. Rong-Hua Wang & Wei-Wei Xu & Hongli Wu & Yue Li & Jiang-Fei Li & Tao Zhang & Genping Huang & Mengchun Ye, 2022. "Ni-catalyzed benzylic β-C(sp3)–H bond activation of formamides," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    12. Yajun Zou & Sara Abednatanzi & Parviz Gohari Derakhshandeh & Stefano Mazzanti & Christoph M. Schüßlbauer & Daniel Cruz & Pascal Voort & Jian-Wen Shi & Markus Antonietti & Dirk M. Guldi & Aleksandr Sav, 2022. "Red edge effect and chromoselective photocatalysis with amorphous covalent triazine-based frameworks," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    13. Ting Wan & Luca Capaldo & Jonas Djossou & Angela Staffa & Felix J. Zwart & Bas Bruin & Timothy Noël, 2024. "Rapid and scalable photocatalytic C(sp2)–C(sp3) Suzuki−Miyaura cross-coupling of aryl bromides with alkyl boranes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    14. Qi-Jun Yao & Fan-Rui Huang & Jia-Hao Chen & Bing-Feng Shi, 2024. "Nickel(II)/BINOL-catalyzed enantioselective C–H activation via desymmetrization and kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-9, 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_s41467-022-29984-0. 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.