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
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] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [2] HOMOLEPTIC CARBENE SILVER(I) AND CARBENE COPPER(I) COMPLEXES
    ARDUENGO, AJ
    DIAS, HVR
    CALABRESE, JC
    DAVIDSON, F
    [J]. ORGANOMETALLICS, 1993, 12 (09) : 3405 - 3409
  • [3] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    Campeau, LC
    Fagnou, K
    [J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
  • [4] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
    Daugulis, Olafs
    Do, Hien-Quang
    Shabashov, Dmitry
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086
  • [5] CARBON NITROGEN CLEAVAGE AND CARBON CARBON COUPLING PROCESSES IN THE REACTIONS OF RU3(CO)12 WITH TERTIARY-AMINES
    DAY, M
    HAJELA, S
    HARDCASTLE, KI
    MCPHILLIPS, T
    ROSENBERG, E
    BOTTA, M
    GOBETTO, R
    MILONE, L
    OSELLA, D
    GELLERT, RW
    [J]. ORGANOMETALLICS, 1990, 9 (04) : 913 - 924
  • [6] Coinage metal catalyzed C-H bond functionalization of hydrocarbons
    Diaz-Requejo, M. Mar
    Perez, Pedro J.
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3379 - 3394
  • [7] Cationic copper(I) complexes as efficient precatalysts for the hydrosilylation of carbonyl compounds
    Díez-González, S
    Scott, NM
    Nolan, SP
    [J]. ORGANOMETALLICS, 2006, 25 (09) : 2355 - 2358
  • [8] Díez-González S, 2008, ALDRICHIM ACTA, V41, P43
  • [9] Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
  • [10] 2-6