A highly efficient heterogeneous copper-catalyzed three-component coupling of tetrahydroisoquinolines, aldehydes and 1-alkynes

被引：58
|
作者：
Zhao, Hong [1 ,2 ,3 ]
He, Wen [1 ,2 ]
Wei, Li [1 ,2 ]
Cai, Mingzhong [1 ,2 ]
机构：
[1] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Peoples R China
[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[3] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
来源：
CATALYSIS SCIENCE & TECHNOLOGY | 2016年 / 6卷 / 05期
基金：
中国国家自然科学基金;
关键词：
MESOPOROUS MOLECULAR-SIEVES; H BONDS ADJACENT; OXIDATIVE MANNICH REACTION; NITROGEN ATOM; ISOQUINOLINE ALKALOIDS; TERMINAL ALKYNES; TERTIARY-AMINES; RECENT PROGRESS; VISIBLE-LIGHT; FUNCTIONALIZATION;
D O I：
10.1039/c5cy01342a
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A highly efficient heterogeneous three-component coupling of tetrahydroisoquinolines, aldehydes and 1-alkynes was achieved in toluene at 70 degrees C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-supported copper(I) complex [MCM-41-2N-CuI], yielding a variety of C1-alkynylated tetrahydroisoquinolines (endo-yne-THIQs) in good to excellent yields with high regioselectivity. This heterogeneous copper catalyst can be easily prepared by a simple two-step procedure from commercially available and inexpensive reagents, and recovered by a simple filtration and reused for at least 10 times without any decrease in activity.
引用
收藏
页码：1488 / 1495
页数：8
相关论文
共 50 条
  • [21] Propargylic amines constructed via copper-catalyzed three-component coupling of terminal alkynes, benzal halides and amines
    Lin, Zhewang
    Yu, Dingyi
    Zhang, Yugen
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4967 - 4970
  • [22] Copper-catalyzed three-component oxycyanation of alkenes
    Zeng, Yuehua
    Li, Yajun
    Lv, Daqi
    Bao, Hongli
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (05) : 908 - 914
  • [23] Copper-catalyzed four-component coupling between aldehydes, amines, alkynes, and carbon dioxide
    Yoo, Woo-Jin
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) : 1503 - 1506
  • [24] Copper-catalyzed three-component reaction of N-heteroaryl aldehydes, nitriles, and water
    Bao, Hanyang
    Zhou, Bingwei
    Jin, Hongwei
    Liu, Yunkui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 5021 - 5028
  • [25] Highly efficient synthesis of furan-2-ylmethylboranes by a copper-catalyzed three-component cascade strategy
    Hang, Chengrui
    Lu, Fei
    Song, Daan
    Wang, Guanghui
    Zhao, Ximei
    NEW JOURNAL OF CHEMISTRY, 2025, 49 (08) : 3006 - 3009
  • [26] Copper-catalyzed 1,1-difunctionalization of terminal alkynes: a three-component reaction for the construction of vinyl sulfones
    Qi Sun
    Linge Li
    Liyan Liu
    Yu Yang
    Zhenggen Zha
    Zhiyong Wang
    Science China Chemistry, 2019, 62 : 904 - 908
  • [27] Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides
    Chen, Yiding
    Murray, Philip R. D.
    Davies, Alyn T.
    Willis, Michael C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (28) : 8781 - 8787
  • [28] Copper-catalyzed, Three-component Polymerization for the Synthesis of Polyphosphonylamidines
    Wang, Wei-hu
    He, Jun-nan
    Zheng, Yu-bin
    Zheng, Nan
    ACTA POLYMERICA SINICA, 2021, 52 (09): : 1129 - 1137
  • [29] Copper-catalyzed 1,1-difunctionalization of terminal alkynes: a three-component reaction for the construction of vinyl sulfones
    Qi Sun
    Linge Li
    Liyan Liu
    Yu Yang
    Zhenggen Zha
    Zhiyong Wang
    Science China(Chemistry), 2019, 62 (07) : 904 - 908
  • [30] Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction
    Li, Ziyong
    Sun, Jiangtao
    ORGANIC LETTERS, 2021, 23 (09) : 3706 - 3711
12345