Copper Promoted C-N and C-O Type Cross-Coupling Reactions

被引:42
|
作者
Das, Pralay [1 ]
Sharma, Dharminder [1 ]
Kumar, Manish [1 ]
Singh, Bikram [1 ]
机构
[1] IHBT CSIR, Nat Plant Prod Div, Palampur 176061, Himachal Prades, India
关键词
CATALYZED ELECTROPHILIC AMINATION; DIARYL ETHER SYNTHESIS; ARYL HALIDES; BOND FORMATION; HIGHLY EFFICIENT; ARYLBORONIC ACIDS; CUPRIC ACETATE; BIARYL ETHER; AMINO-ACID; ULLMANN CONDENSATION;
D O I
10.2174/138527210791111830
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryl amines and ethers are very important structural motifs of numerous biologically active natural products, important pharmaceutical compounds, polymers in the material science industries and widely used as drugs, dyes, and other fine chemicals. Several studies have earlier been attempted but transition metal mediated protocols have proven more successful results. Conventional Ullmann condensation with copper in the form of metal, alloy or Cu(I)/Cu(II) salt showed major drawbacks such as requirement of high temperature sensitivity to catalyst-type and low to moderate yield. In recent years, copper promoted conventional Ullmann condensation reactions have been improved a lot under ligand and ligand free conditions with excellent conversion. An important Ullmann type coupling, where aryl boronic acids are used as arylating agents instead of aryl halides has recently attracted much attention of chemist. Because of the importance of aryl amines and ethers in various fields of chemistry writing a review in this relevant area is of significant interest. This article will review the applications of copper-promoted C-N and C-O bond formation reactions focused on achievements during the periods from 2000-2008.
引用
收藏
页码:754 / 783
页数:30
相关论文
共 50 条
  • [1] CuO Nanoparticles Catalyzed C-N, C-O, and C-S Cross-Coupling Reactions: Scope and Mechanism
    Jammi, Suribabu
    Sakthivel, Sekarpandi
    Rout, Laxmidhar
    Mukherjee, Tathagata
    Mandal, Santu
    Mitra, Raja
    Saha, Prasenjit
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) : 1971 - 1976
  • [2] Maghemite-Copper Nanocomposites: Applications for Ligand-Free Cross-Coupling (C-O, C-S, and C-N) Reactions
    Sharma, Rakesh K.
    Gaur, Rashmi
    Yadav, Manavi
    Rathi, Anuj K.
    Pechousek, Jiri
    Petr, Martin
    Zboril, Radek
    Gawande, Manoj B.
    CHEMCATCHEM, 2015, 7 (21) : 3495 - 3502
  • [3] An in situ generated CuI/metformin complex as a novel and efficient catalyst for C-N and C-O cross-coupling reactions
    Ghorbani-Vaghei, Ramin
    Hemmati, Saba
    Veisi, Hojat
    TETRAHEDRON LETTERS, 2013, 54 (52) : 7095 - 7099
  • [4] Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions
    Monnier, Florian
    Taillefer, Marc
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) : 6954 - 6971
  • [5] Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C-N and C-O cross-coupling reactions
    Hajipour, Abdol R.
    Check, Maryam
    Khorsandi, Zahra
    APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (11)
  • [6] Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles
    Saha, Prasenjit
    Ali, Md Ashif
    Ghosh, Pokhraj
    Punniyamurthy, Tharmalingam
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5692 - 5699
  • [7] On-DNA Pd and Cu promoted C-N cross-coupling reactions
    Lu, Xiaojie
    Roberts, Sarah E.
    Franklin, George J.
    Davie, Christopher P.
    MEDCHEMCOMM, 2017, 8 (08) : 1614 - 1617
  • [8] Green Cross-Coupling Using Visible Light for C-O and C-N Bond Formation
    Yi, Hong
    Liu, Yichang
    Lei, Aiwen
    ORGANOMETALLICS FOR GREEN CATALYSIS, 2019, 63 : 266 - 293
  • [9] Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation
    Bhunia, Subhajit
    Pawar, Govind Goroba
    Kumar, S. Vijay
    Jiang, Yongwen
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) : 16136 - 16179
  • [10] Mesoporous nitrogen-doped carbon for copper-mediated Ullmann-type C-O/-N/-S cross-coupling reactions
    Zhang, Pengfei
    Yuan, Jiayin
    Li, Haoran
    Liu, Xiaofeng
    Xu, Xuan
    Antonietti, Markus
    Wang, Yong
    RSC ADVANCES, 2013, 3 (06) : 1890 - 1895