Nitrooxylative Dearomatization Reaction of β-Naphthols with Hypervalent Iodine Reagent

被引:3
|
作者
Zhang, Shan-Shan [1 ,2 ]
Li, Muzi [2 ]
Gu, Qing [2 ]
You, Shu-Li [1 ,2 ]
机构
[1] East China Normal Univ, Chang Kung Chuang Inst, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, New Cornerstone Sci Lab, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
dearomatization; hypervalent iodine reagent; beta-naphthol; nitrooxylative; ASYMMETRIC ALLYLIC DEAROMATIZATION; TERT-BUTYL NITRITE; OXIDATIVE DEAROMATIZATION; ARYLATIVE DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; NITRATE; OXIDE; 2-NAPHTHOLS; EFFICIENT; ALCOHOLS;
D O I
10.1002/ajoc.202400005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalyst-free intermolecular dearomatization reaction of beta-naphthols with hypervalent-iodine-based nitrooxylating reagent is reported. Various nitrooxylated beta-naphthalenones bearing a quaternary carbon stereogenic center were obtained smoothly in good to excellent yields (up to 87 %) under mild conditions. This method features mild conditions, broad substrate scope and excellent chemoselectivity.
引用
收藏
页数:4
相关论文
共 50 条
  • [21] Stepwise Mechanism for the Bromination of Arenes by a Hypervalent Iodine Reagent
    Granados, Albert
    Shafir, Alexandr
    Arrieta, Ana
    Cossio, Fernando P.
    Vallribera, Adelina
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 2142 - 2150
  • [22] Alkynylation of heterocyclic compounds using hypervalent iodine reagent
    Kamlar, M.
    Cisarova, I.
    Vesely, J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2884 - 2889
  • [23] N-GLYCOSYLATION REACTION OF THIO-GLYCOSIDE USING HYPERVALENT IODINE(III) REAGENT
    Morimoto, Koji
    Yanase, Kana
    Ikeda, Takumi
    Uchikawa, Chihiro
    Kita, Yasuyuki
    Kajimoto, Tetsuya
    HETEROCYCLES, 2020, 101 (02) : 621 - 630
  • [24] Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(III) reagent
    Tohma, H
    Iwata, M
    Maegawa, T
    Kita, Y
    TETRAHEDRON LETTERS, 2002, 43 (50) : 9241 - 9244
  • [25] Oxidative biaryl coupling reaction of phenol ether derivatives using a hypervalent iodine(III) reagent
    Takada, T
    Arisawa, M
    Gyoten, M
    Hamada, R
    Tohma, H
    Kita, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22): : 7698 - 7706
  • [26] Mechanistic Insight into Phenol Dearomatization by Hypervalent Iodine: Direct Detection of a Phenoxenium Cation
    Juneau, Antoine
    Lepage, Iannick
    Sabbah, Sami G.
    Winter, Arthur H.
    Frenette, Mathieu
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14274 - 14283
  • [27] Hypervalent Iodine-Mediated Regioselective Dearomatization of Non-Activated Arenes
    Wang, Yang
    Yin, Ji-Chen
    Zhang, Yu-Wei
    Zhang, Yuzhe
    Shi, Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (20) : 4253 - 4259
  • [28] Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization
    El Assal, Mourad
    Peixoto, Philippe A.
    Coffinier, Romain
    Gamier, Tony
    Deffieux, Denis
    Miqueu, Karinne
    Sotiropoulos, Jean-Marc
    Pouysegu, Laurent
    Quideau, Stephane
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22): : 11816 - 11828
  • [29] Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents
    Zhang, Huaiyaun
    Xu, Nuo
    Tang, Rongping
    Shi, Xingli
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (11) : 3784 - 3805
  • [30] Recent Computational Studies on Mechanisms of Hypervalent Iodine(III)-Promoted Dearomatization of Phenols
    Zheng, Hanliang
    Xue, Xiao-Song
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (18) : 2106 - 2117