ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Efficient Synthesis of α-Allylbutenolides from Allyl Ynoates via Tandem Ligand-Enabled Au(I) Catalysis and the Claisen Rearrangement

  • Huiyan Wang
    Huiyan Wang
    Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
    School of Chemical Engineering, Jiangsu Ocean University, Lianyungang, Jiangsu 222005, People’s Republic of China
    More by Huiyan Wang
  • Ting Li
    Ting Li
    Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
    More by Ting Li
  • Zhitong Zheng
    Zhitong Zheng
    Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
  • , and 
  • Liming Zhang*
    Liming Zhang
    Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
    *E-mail: [email protected]
    More by Liming Zhang
Cite this: ACS Catal. 2019, 9, 11, 10339–10342
Publication Date (Web):October 17, 2019
https://doi.org/10.1021/acscatal.9b03501
Copyright © 2019 American Chemical Society

    Article Views

    3251

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    A facile construction of α-allylbutenolides from readily available allyl ynoates has been developed via tandem gold-catalyzed alkyne isomerization to allene and cycloisomerization, the Claisen rearrangement and a double bond migration. The gold catalysis is enabled by a bifunctional phosphine ligand featuring a critical remote tertiary amino group, and the reaction tolerates a range of substituents and exhibits yields up to 96%.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.9b03501.

    • Experimental procedures, characterization data including 1H and 13C NMR spectra, IR spectra and HR-MS, and copies of NMR spectra (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 19 publications.

    1. Chenlin Lu, Xue Peng, Basudev Maity, Xiang Sheng, Yinhuan Zhou, Takafumi Ueno, Zheng Liu, Diannan Lu. Novel Au(I)-Based Artificial Metallo-Cycloisomerase for Catalyzing the Cycloisomerization of γ-Alkynoic Acids. ACS Catalysis 2023, 13 (15) , 9918-9924. https://doi.org/10.1021/acscatal.3c01197
    2. Zipeng Wang, Tongxiang Cao, Shifa Zhu. Gold-Catalyzed Enynal and Enynol Coupling by Selectively Steering Two Transient Vinyl-Gold Intermediates. Organic Letters 2022, 24 (50) , 9296-9300. https://doi.org/10.1021/acs.orglett.2c03890
    3. Ting Li, Shicheng Dong, Conghui Tang, Meiling Zhu, Nan Wang, Weiguang Kong, Wenchao Gao, Jun Zhu, Liming Zhang. Asymmetric Construction of α,γ-Disubstituted α,β-Butenolides Directly from Allylic Ynoates Using a Chiral Bifunctional Phosphine Ligand Enables Cooperative Au Catalysis. Organic Letters 2022, 24 (24) , 4427-4432. https://doi.org/10.1021/acs.orglett.2c01652
    4. Fangfang Lu, Yangxu Chen, Xue Song, Chenxia Yu, Tuanjie Li, Kai Zhang, Changsheng Yao. NHC-Catalyzed [2 + 4] Annulation of Alkynyl Ester with Chalcone. The Journal of Organic Chemistry 2022, 87 (10) , 6902-6909. https://doi.org/10.1021/acs.joc.2c00022
    5. Hongyu Guo, Sheng Zhang, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao. [3 + 2] Cycloaddition of α-Aryl-α-diazoacetates with Terminal Alkynes via the Cooperative Catalysis of Palladium and Acid. ACS Catalysis 2021, 11 (17) , 10789-10795. https://doi.org/10.1021/acscatal.1c02533
    6. Christoph M. Hendrich, Kohei Sekine, Takumi Koshikawa, Ken Tanaka, A. Stephen K. Hashmi. Homogeneous and Heterogeneous Gold Catalysis for Materials Science. Chemical Reviews 2021, 121 (14) , 9113-9163. https://doi.org/10.1021/acs.chemrev.0c00824
    7. Chetan C. Chintawar, Amit K. Yadav, Anil Kumar, Shashank P. Sancheti, Nitin T. Patil. Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control. Chemical Reviews 2021, 121 (14) , 8478-8558. https://doi.org/10.1021/acs.chemrev.0c00903
    8. Xinpeng Cheng, Tianyou Li, Kaylaa Gutman, Liming Zhang. Chiral Bifunctional Phosphine Ligand-Enabled Cooperative Cu Catalysis: Formation of Chiral α,β-Butenolides via Highly Enantioselective γ-Protonation. Journal of the American Chemical Society 2021, 143 (29) , 10876-10881. https://doi.org/10.1021/jacs.1c05781
    9. Ting Li, Yuhan Yang, Baomin Luo, Bo Li, Luyi Zong, Weiguang Kong, Hao Yang, Xinpeng Cheng, Liming Zhang. A Bifunctional Ligand Enables Gold-Catalyzed Hydroarylation of Terminal Alkynes under Soft Reaction Conditions. Organic Letters 2020, 22 (15) , 6045-6049. https://doi.org/10.1021/acs.orglett.0c02130
    10. Li‐Cai Liu, Shuang Lin, Kangwei Xu, Jiasheng Qian, Ruibo Wu, Qingjiang Li, Honggen Wang. NHC‐Au‐Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3‐Dienes. Advanced Science 2024, 47 https://doi.org/10.1002/advs.202308710
    11. Yuzhi Wang, Yadong Yu, Yang Yu, Fei Huang, Jonathan B. Baell. Copper‐Catalyzed Olefinic C( sp 2 )−H Activation/Carbene Insertion/Ester Hydrolysis/Cyclization with Aryl Diazo Esters for the Synthesis of Multisubstituted Furanones. Advanced Synthesis & Catalysis 2023, 365 (15) , 2601-2606. https://doi.org/10.1002/adsc.202300494
    12. V. D. Dyachenko, B. N. Baryshev, V. G. Nenajdenko. [3,3]-Sigmatropic rearrangements: a variety of methods and recent advances. Russian Chemical Reviews 2022, 91 (8) , RCR5039. https://doi.org/10.1070/RCR5039
    13. Huijin Lee, Ki Tae Kim, Min Kim, Cheoljae Kim. Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements. Catalysts 2022, 12 (2) , 227. https://doi.org/10.3390/catal12020227
    14. Giuseppe Zuccarello, Imma Escofet, Ulysse Caniparoli, Antonio M. Echavarren. New‐Generation Ligand Design for the Gold‐Catalyzed Asymmetric Activation of Alkynes. ChemPlusChem 2021, 86 (9) , 1283-1296. https://doi.org/10.1002/cplu.202100232
    15. Ming Bao, Xiongda Xie, Wenhao Hu, Xinfang Xu. Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[ c ]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes. Advanced Synthesis & Catalysis 2021, 363 (16) , 4018-4023. https://doi.org/10.1002/adsc.202100602
    16. Imtiaz Khan, Aliya Ibrar, Sumera Zaib. Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges. Topics in Current Chemistry 2021, 379 (1) https://doi.org/10.1007/s41061-020-00316-4
    17. Ting Li, Xinpeng Cheng, Pengcheng Qian, Liming Zhang. Gold-catalysed asymmetric net addition of unactivated propargylic C–H bonds to tethered aldehydes. Nature Catalysis 2021, 4 (2) , 164-171. https://doi.org/10.1038/s41929-020-00569-8
    18. Xiaojun Hu, Bingwei Zhou, Hongwei Jin, Yunkui Liu, Liming Zhang. Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans. Chemical Communications 2020, 56 (53) , 7297-7300. https://doi.org/10.1039/D0CC01238F
    19. Giuseppe Zuccarello, Margherita Zanini, Antonio M. Echavarren. Buchwald‐Type Ligands on Gold(I) Catalysis. Israel Journal of Chemistry 2020, 60 (3-4) , 360-372. https://doi.org/10.1002/ijch.201900179

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect