IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-30006-2.html
   My bibliography  Save this article

Regio- and enantioselective remote hydroarylation using a ligand-relay strategy

Author

Listed:
  • Yuli He

    (Nanjing University)

  • Jiawei Ma

    (Nanjing University)

  • Huayue Song

    (Nanjing University)

  • Yao Zhang

    (Nanjing University)

  • Yong Liang

    (Nanjing University)

  • You Wang

    (Nanjing University)

  • Shaolin Zhu

    (Nanjing University
    Henan Normal University)

Abstract

The design of a single complicated chiral ligand to well-promote each step of an asymmetric cascade reaction is sometimes a formidable challenge in transition metal catalysis. In this work, a highly regio- and enantioselective Ni-catalysed migratory hydroarylation relay process has been achieved with the combination of two simple ligands, one which accomplishes chain-walking and the other causing asymmetric arylation. This formal asymmetric C(sp3)−H arylation provides direct access to a wide range of structurally diverse chiral 1,1-diarylalkanes, a structural unit found in a number of bioactive molecules. The value of this strategy was further demonstrated by the Ni-catalysed migratory asymmetric 1,3-arylboration.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30006-2
    DOI: 10.1038/s41467-022-30006-2
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-30006-2
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-30006-2?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. "Erratum: Recent advances in homogeneous nickel catalysis," Nature, Nature, vol. 510(7503), pages 176-176, June.
    2. 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.
    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. 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.
    7. 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.
    8. 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.
    9. 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.
    10. 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.
    11. 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.
    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.

    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_s41467-022-30006-2. 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.