Facile C-N Bond Cleavage Promoted by Cuprous Oxide: Formation of C-C-Coupled Biimidazole from Its Methylene-Bridged Congener

被引：39
|
作者：
Sabiah, Shahulhameed [1 ]
Lee, Chen-Shiang [1 ]
Hwang, Wen-Shu [1 ]
Lin, Ivan J. B. [1 ]
机构：
[1] Natl Dong Hwa Univ, Dept Chem, Hualien 974, Taiwan
来源：
ORGANOMETALLICS | 2010年 / 29卷 / 02期
关键词：
CARBON-NITROGEN BOND; HETEROCYCLIC CARBENE COMPLEXES; CRYSTAL-STRUCTURES; HIGHLY EFFICIENT; PALLADIUM; LIGANDS; DERIVATIVES; ACTIVATION; ARYLATION; CATALYSTS;
D O I：
10.1021/om9010406
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The methylenebis(N-alkylimidazolium) halides are converted to dialkylbiimidazoles by cuprous oxide wit concurrent C-N bond cleavage and C-C bond formation. This unusual C-N bond cleavage is proposed to involve a Cu(I)-NHC (N-heterocyclic carbene) complex. The reaction is unique, as it involves C-H bond activation, C-N bond cleavage, and C-C bond formation.
引用
收藏
页码：290 / 293
页数：4
相关论文
共 50 条
  • [1] Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
    Wang, Min
    Lu, Jianmin
    Ma, Jiping
    Zhang, Zhe
    Wang, Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14061 - 14065
  • [2] Facile C-N cleavage in a series of bridged lactams
    Lei, Y
    Wrobleski, AD
    Golden, JE
    Powell, DR
    Aubé, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4552 - 4553
  • [3] A vanadium-promoted C-N bond cleavage
    Egdal, RK
    Larsen, FB
    Bond, AD
    McKenzie, CJ
    INORGANICA CHIMICA ACTA, 2005, 358 (02) : 376 - 382
  • [4] Photochemical Formation and Cleavage of C-N Bond
    Wang, Pengfei
    Lu, Wenya
    Devalankar, Dattatray
    Ding, Zhenying
    ORGANIC LETTERS, 2015, 17 (01) : 170 - 172
  • [5] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [6] Amide C-N bond cleavage and formation of nitride promoted by a Niobium(II) cluster
    Tayebani, M
    Feghali, H
    Gambarotta, S
    Bensimon, C
    ORGANOMETALLICS, 1997, 16 (23) : 5084 - 5088
  • [7] Transition-metal-free and base promoted C-C bond formation via C-N bond cleavage of organoammonium salts
    Zhang, Tao
    Wang, Kunyu
    Ke, Yuting
    Tang, Yuanyuan
    Liu, Long
    Huang, Tianzeng
    Li, Chunya
    Tang, Zhi
    Chen, Tieqiao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8237 - 8240
  • [8] Copper-catalyzed and iodide-promoted aerobic C-C bond cleavage/C-N bond formation toward the synthesis of amides
    Wu, Kun
    Huang, Zhiliang
    Ma, Yiyang
    Lei, Aiwen
    RSC ADVANCES, 2016, 6 (29): : 24349 - 24352
  • [9] C-H versus C-N bond cleavage promoted by Niobium(II) amide
    Tayebani, M
    Gambarotta, S
    Yap, G
    ORGANOMETALLICS, 1998, 17 (17) : 3639 - 3641
  • [10] Electrochemical Oxidative C-C Bond Cleavage of Ketones for C-N Bond Formation: A Route to Amides
    He, Yonghui
    Zeng, Liang
    Li, Ming
    Gu, Lijun
    Zhang, Shengyong
    Li, Ganpeng
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (19): : 12622 - 12631
12345