Pd(0)-Catalyzed intramolecular arylative dearomatization of β-naphthols

被引:42
|
作者
Xu, Ren-Qi [1 ]
Yang, Ping [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Univ Chinese Acad Sci, 345 Lingling Lu, Shanghai 200032, Peoples R China
关键词
CATALYTIC ASYMMETRIC DEAROMATIZATION; HYDROXYLATIVE PHENOL DEAROMATIZATION; ENANTIOSELECTIVE DEAROMATIZATION; OXIDATIVE DEAROMATIZATION; CONSTRUCTION; EFFICIENT; INDOLES; GOLD; ACCESS; SKELETON;
D O I
10.1039/c7cc04022a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient Pd(0)-catalyzed intramolecular arylative dearomatization of beta-naphthols is described. Using Q-Phos as a ligand, the arylative dearomatization reaction proceeded smoothly affording excellent yields and chemoselectivity even when the catalyst loading was reduced to 0.1 mol%. This method offers an efficient access to a series of structurally diverse spirocarbocycles. Preliminary investigation indicates that an enantioselective reaction is feasible in the presence of a chiral phosphoramidite ligand.
引用
收藏
页码:7553 / 7556
页数:4
相关论文
共 50 条
  • [21] Ni-Catalyzed Allylic Dearomatization Reaction of β-Naphthols with Allylic Alcohols
    Zhang, Hui-Jun
    Gu, Qing
    You, Shu-Li
    ORGANIC LETTERS, 2020, 22 (08) : 3297 - 3301
  • [22] A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy
    Dhineshkumar, Jayaraman
    Samaddar, Prasanjit
    Prabhu, Kandikere Ramaiah
    CHEMICAL COMMUNICATIONS, 2016, 52 (74) : 11084 - 11087
  • [23] Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols
    Heid, Berenice
    Plietker, Bernd
    SYNTHESIS-STUTTGART, 2016, 48 (03): : 340 - 350
  • [24] Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of Naphthols with Quinones
    Zhu, Gongming
    Bao, Guangjun
    Li, Yiping
    Yang, Junxian
    Sun, Wangsheng
    Li, Jing
    Hong, Liang
    Wang, Rui
    ORGANIC LETTERS, 2016, 18 (20) : 5288 - 5291
  • [25] Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Substituted β-Naphthols with Morita-Baylis-Hillman (MBH) Adducts
    Zhang, Qing-Xia
    Gu, Qing
    You, Shu-Li
    ORGANIC LETTERS, 2022, 24 (43) : 8031 - 8035
  • [26] Palladium-Catalyzed Arylative Dearomatization and Subsequent Aromatization/Dearomatization/Aza-Michael Addition: Access to Zephycarinatine and Zephygranditine Skeletons
    Liu, Chao
    Song, Liangliang
    Van Meervelt, Luc
    Peshkov, Vsevolod A.
    Li, Zhenghua
    Van der Eycken, Erik V.
    ORGANIC LETTERS, 2021, 23 (13) : 5065 - 5070
  • [27] Rhodium-Catalyzed Intramolecular Difluoromethylenative Dearomatization of Phenols
    Li, Yajun
    Zhang, Lisi
    Zhang, Li
    Wu, Yongming
    Gong, Yuefa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (35) : 8039 - 8047
  • [28] Pd(II)-Catalyzed Asymmetric C-H Functionalization/Dearomatization of Naphthols through Axial-to-Central Chirality Transfer
    Kong, Ke-Xin
    Zhou, Tao
    Yuan, Wen-Kui
    Hui, Xin-Shang
    Li, Ya
    Shi, Bing-Feng
    ACS CATALYSIS, 2025, 15 (05): : 4280 - 4286
  • [29] Pd(0)-catalyzed chemoselective construction of spirocarbocycles via an alkyne insertion/β-naphthol dearomatization cascade
    Zheng, Huayu
    Bai, Lu
    Liu, Jingjing
    Nan, Jiang
    Zuo, Zhijun
    Yang, Liu
    Wang, Yaoyu
    Luan, Xinjun
    CHEMICAL COMMUNICATIONS, 2015, 51 (15) : 3061 - 3064
  • [30] Acid-Catalyzed [4+1]-Dearomatization Spiroannulation of Hydroquinones and Naphthols
    Ding, Nan
    Li, Zhi
    SYNLETT, 2023, 34 (20) : 2417 - 2422