國家衛生研究院 NHRI:Item 3990099045/16436
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    题名: Generation of quaternary carbons in cycloalkanones and lactones with arynes through a domino process
    作者: Hwu, JR;Bohara, KP;Kapoor, M;Roy, A;Lin, SY;Lin, CC;Hwang, KC;Huang, WC;Tsay, SC
    贡献者: Institute of Biotechnology and Pharmaceutical Research
    摘要: A synthetic method was developed for the generation of a quaternary carbon center in carbonyl compounds. This innovative process involved the reaction of alpha-thiolate lactones and cycloalkanones with two equivalents of arynes in acetonitrile to give alpha,alpha-diarylated products in 63-85% yields at 25 degrees C. The reaction unfolds through an unconventional domino process, encompassing sequential 1,2-elimination, 1,2-nucleophilic addition, 1,4-proton transfer, the second 1,2-nucleophilic addition, interrupted Pummerer rearrangement, intramolecular spirocyclization, and sulfonium ring-opening. The potential of this "single-flask" reaction was systematically investigated and found well-suited to generate diarylated carbonyl compounds, incorporating naphthalene, pyridine, quinoline, or isoquinoline rings adorned with various substituents.
    日期: 2024-11-30
    關聯: Journal of Organic Chemistry. 2024 Nov 30;89(24):18393-18399.
    Link to: http://dx.doi.org/10.1021/acs.joc.4c02257
    JIF/Ranking 2023: http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=&DestApp=IC2JCR
    Cited Times(WOS): https://www.webofscience.com/wos/woscc/full-record/WOS:001367668100001
    Cited Times(Scopus): https://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85210532492
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