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
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 04期
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
  • [41] Alkoxylation Followed by Iodination of Oxindole with Alcohols Mediated by Hypervalent Iodine Reagent in the Presence of Iodine
    Kotagiri, Rajendraprasad
    Adepu, Ramesh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (33) : 4556 - 4564
  • [42] DFT mechanistic investigation into phenol dearomatization mediated by an iodine(iii) reagent
    Ganji, Babak
    Ariafard, Alireza
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (14) : 3521 - 3528
  • [43] Synthesis of fluorinated polycyclic dehydroaltenusin analogs through hypervalent iodine-catalyzed dearomatization
    Cao, Jiaqi
    Deng, Qingfu
    Hu, Liangzhen
    Zhang, Xiaohui
    Xiong, Yan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8104 - 8107
  • [44] DFT mechanistic investigation into phenol dearomatization mediated by an iodine(iii) reagent
    Ganji B.
    Ariafard A.
    Organic and Biomolecular Chemistry, 2019, 17 (14): : 3521 - 3528
  • [45] A rapid access to hydroxylated benz[a]anthraquinones: Hypervalent iodine oxidation of beta-naphthols
    Mal, D
    Roy, HN
    Hazra, NK
    Adhikari, S
    TETRAHEDRON, 1997, 53 (06) : 2177 - 2184
  • [46] Organic synthesis using a hypervalent iodine reagent: unexpected and novel domino reaction leading to spiro cyclohexadienone lactones
    Fujioka, Hiromichi
    Komatsu, Hideyuki
    Nakamura, Taeko
    Miyoshi, Akihito
    Hata, Kayoko
    Ganesh, Jnashuara
    Murai, Kenichi
    Kita, Yasuyuki
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4133 - 4135
  • [47] Asymmetric Dearomatization of β-Naphthols through an Amination Reaction Catalyzed by a Chiral Phosphoric Acid
    Wang, Shou-Guo
    Yin, Qin
    Zhuo, Chun-Xiang
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 647 - 650
  • [48] Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction
    Wang, Shou-Guo
    Liu, Xi-Jia
    Zhao, Qun-Chao
    Zheng, Chao
    Wang, Shao-Bo
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14929 - 14932
  • [49] Polymer-supported hypervalent iodine reagent mediated synthesis of α-azidoketones
    Wang, Huey-Min
    Hou, Rei-Sheu
    Wu, Jian-Long
    Chen, Ling-Ching
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (05) : 1333 - 1335
  • [50] CYCLODEHYDROGENATION OF 2'-HYDROXYCHALCONES WITH HYPERVALENT IODINE REAGENT - A NEW SYNTHESIS OF FLAVONES
    LITKEI, G
    GULACSI, K
    ANTUS, S
    BLASKO, G
    LIEBIGS ANNALEN, 1995, (09): : 1711 - 1715
12345