Palladium-Catalyzed One-Pot Consecutive Amination and Sonogashira Coupling for Selective Synthesis of 2-Alkynylanilines

被引：58
|
作者：
Pan, Shanfei [1 ]
Ma, Xueji [1 ]
Zhong, Danni [1 ]
Chen, Wanzhi [1 ]
Liu, Miaochang [2 ]
Wu, Huayue [2 ]
机构：
[1] Hangzhou Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325027, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 14-15期
关键词：
alkynols; 2-alkynylanilines; norbornene; palladium; tandem reactions; TOSYLHYDRAZONE INSERTION REACTION; C-H ACTIVATION; SUBSTITUTED ARYL IODIDES; ALPHA; ALPHA-DISUBSTITUTED ARYLMETHANOLS; EFFICIENT SYNTHESIS; INDOLE ALKALOIDS; BOND-CLEAVAGE; O-TERARYLS; SEQUENCE; ROUTE;
D O I：
10.1002/adsc.201500381
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient catalytic approach to the synthesis of N,N-dialkyl-2-alkynylanilines was developed by using Pd-catalyzed norbornene-mediated three-component reactions of haloarenes, alkoxyamines (RO-NR2), and alkynes. The procedure forms one C N bond and one C C bond efficiently in a one-pot manner from readily available starting materials. A number of 2-alkynylanilines with a broad range of functional groups were afforded in good to excellent yields.
引用
收藏
页码：3052 / 3056
页数：5
相关论文
共 50 条
  • [1] One-Pot Gold-Catalyzed Aminofluorination of Unprotected 2-Alkynylanilines
    Arcadi, Antonio
    Pietropaolo, Emanuela
    Alvino, Antonello
    Michelet, Veronique
    ORGANIC LETTERS, 2013, 15 (11) : 2766 - 2769
  • [2] Palladium-Catalyzed Decarboxylative Coupling of Alkynoic Acids with 2-Alkynylanilines in Ionic Liquid
    Lai, Yin-Long
    Xiong, Xun
    Zhao, Ting
    Li, Jianxiao
    Zhong, Rui-Min
    Xiong, Wenfang
    Jiang, Huanfeng
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [3] One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source
    Xiong, Wenfang
    Wu, Bowen
    Zhu, Baiyao
    Tan, Xiaobin
    Wang, Lu
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    CHEMCATCHEM, 2021, 13 (12) : 2843 - 2851
  • [4] ONE-POT PALLADIUM-CATALYZED SYNTHESIS OF DIARYLALKYNES
    CARPITA, A
    LESSI, A
    ROSSI, R
    SYNTHESIS-STUTTGART, 1984, (07): : 571 - 572
  • [5] One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
    Jong, Howard
    Eey, Stanley T. -C.
    Lim, Yee Hwee
    Pandey, Sangeeta
    Iqbal, Nurul Azmah Bte
    Yong, Fui Fong
    Robins, Edward G.
    Johannes, Charles W.
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 616 - 622
  • [6] Synthesis of 3-Chloroindoles via Palladium-Catalyzed Chlorocyclization of Unmasked 2-Alkynylanilines
    Zheng, Yongpeng
    Li, Jianxiao
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [7] One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon
    Moon, Jeongju
    Jeong, Miso
    Nam, Hyungoog
    Ju, Jinhun
    Moon, Joong Ho
    Jung, Hyun Min
    Lee, Sunwoo
    ORGANIC LETTERS, 2008, 10 (05) : 945 - 948
  • [8] Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization
    Krishna Reddy, Alavala Gopi
    Satyanarayana, Gedu
    SYNTHESIS-STUTTGART, 2017, 49 (23): : 5149 - 5158
  • [9] One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination
    Lu, Bruce Z.
    Wei, Han-Xun
    Zhang, Yongda
    Zhao, Wenyi
    Dufour, Marine
    Li, Guisheng
    Farina, Vittorio
    Senanayake, Chris H.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09): : 4558 - 4562
  • [10] Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones
    Suchand, Basuli
    Satyanarayana, Gedu
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 372 - 381
12345