Palladium catalyzed synthesis of sugar-fused indolines via C(sp2)-H/N-H activation

被引：7
|
作者：
Verma, Ashish Kumar [1 ]
Chennaiah, Ande [1 ]
Dubbu, Sateesh [1 ]
Vankar, Yashwant D. [1 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
CARBOHYDRATE RESEARCH | 2019年 / 473卷
关键词：
C(sp(2))-H/N-H activation in carbohydrates; Annulated sugars; Sugar-fused indolines; Sugar-fused indoles; C-H ACTIVATION; PD(II)-CATALYZED AMINATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; C(SP(3))-H BONDS; NATURAL-PRODUCTS; CELL-ADHESION; ISOCHROMANS; ACCESS;
D O I：
10.1016/j.carres.2018.12.015
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A simple Pd(OAc)(2) catalyzed strategy for the synthesis of sugar-fused indolines from 2-N-oxalylamido-2-deoxy-C-aryl glycosides is reported by utilizing N-oxalylamido group as an auxiliary via C(sp(2))-H/N-H Activation. The reaction is successfully applied on glucose as well as galactose derived differently substituted 2-N-oxalylamido-2-deoxy-C-aryl glycosides to give sugar-fused indolines in moderate to good yields. The utility of this strategy in the synthesis of sugar-fused indoles is also described.
引用
收藏
页码：57 / 65
页数：9
相关论文
共 50 条
  • [1] Palladium-NHC Catalyzed Enantioselective Synthesis of Fused Indolines via Inert C(sp3)-H Activation
    Nakanishi, Masafumi
    Katayev, Dmitry
    Besnard, Celine
    Kuendig, E. Peter
    CHIMIA, 2012, 66 (04) : 241 - 243
  • [2] Enantioselective palladium-catalyzed C(sp2)-H carbamoylation
    Dong, Wenfeng
    Xu, Guangqing
    Tang, Wenjun
    TETRAHEDRON, 2019, 75 (24) : 3239 - 3247
  • [3] Synthesis of Unsymmetrically Substituted Tetraphenylenes through Palladium-Catalyzed C(sp2)-H Activation
    Wan, Bin
    Zhang, Yanghui
    SYNTHESIS-STUTTGART, 2021, 53 (18): : 3299 - 3306
  • [4] Palladium(II)-Catalyzed Cycloamidination via C(sp2)-H Activation and Isocyanide Insertion
    Wang, Yong
    Zhu, Qiang
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) : 1902 - 1908
  • [5] Palladium-Catalyzed Synthesis of Fluorenes by Intramolecular C(sp2)-H Activation at Room Temperature
    Tanji, Yutaka
    Tsuji, Yasushi
    Fujihara, Tetsuaki
    SYNLETT, 2020, 31 (08) : 805 - 808
  • [6] Palladium-Catalyzed C(sp2)-H Silylation via a Native-Amine- Directed Strategy
    Yan, Yintao
    Wang, Xuan
    Li, Jianhua
    Jiang, Chao
    SYNLETT, 2023, 34 (04) : 369 - 373
  • [7] Synthesis of [60]Fullerene-Fused Tetralones via Palladium-Catalyzed Ketone-Directed sp2 C-H Activation and sp3 C-H Functionalization
    Zhou, Dian-Bing
    Wang, Guan-Wu
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (10) : 1548 - 1554
  • [8] Copper-Catalyzed C(sp2)-C(sp2) Bond Formation via Single C(sp2)-H Activation
    Parmar, Himanshu V.
    Adodariya, Yash J.
    Patel, Unnati P.
    Shrivastav, Pranav S.
    Maru, Jayesh J.
    CHEMISTRYSELECT, 2024, 9 (02):
  • [9] Palladium(II)-catalyzed aerobic intramolecular allylic C-H activation for the synthesis of indolines
    Xu, Changrui
    Wu, Zhengxing
    Chen, Jianzhong
    Xie, Fang
    Zhang, Wanbin
    TETRAHEDRON, 2017, 73 (14) : 1904 - 1910
  • [10] Synthetic advances in C(sp2)-H/N-H arylation of pyrazole derivatives through activation/substitution
    Konwar, Manashjyoti
    Hazarika, Roktopol
    Sarma, Diganta
    TETRAHEDRON, 2021, 102
12345