A state-of-the-art cyanation of aryl bromides:: A novel and versatile copper catalyst system inspired by nature

被引：131

作者：

Schareina, Thomas

Zapf, Alexander

Maegerlein, Wolfgang

Mueller, Nikolaus

Beller, Matthias

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[2] Saltigo GmbH, D-51369 Leverkusen, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2007年 / 13卷 / 21期

关键词：

alkylimidazoles; bromoarenes; copper; cyanation; nitriles;

D O I：

10.1002/chem.200700079

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general protocol for the cyanation of aryl halides with the nontoxic cyanide source K-4[Fe(CN)(6)] using copper catalysis and a ligand system based on 1-alkylimidazoles is presented. The advantages of this system are the high selectivity, a unique substrate range, easy handling, and inexpensive reagents.

引用

页码：6249 / 6254

页数：6

共 42 条

[1] Copper mediates dityrosine cross-linking of Alzheimer's amyloid-β
Atwood, CS
Perry, G
Zeng, H
Kato, Y
Jones, WD
Ling, KQ
Huang, XD
Moir, RD
Wang, DD
Sayre, LM
Smith, MA
Chen, SG
Bush, AI
[J]. BIOCHEMISTRY, 2004, 43 (02) : 560 - 568
[2] A copper(I) protein possibly involved in the assembly of CuA center of bacterial cytochrome c oxidase
Banci, L
Bertini, I
Ciofi-Baffoni, S
Katsari, E
Katsaros, N
Kubicek, K
Mangani, S
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (11) : 3994 - 3999
[3] Catalytic Sandmeyer cyanation as a synthetic pathway to aryl nitriles
Beletskaya, IP
Sigeev, AS
Peregudov, AS
Petrovskii, PV
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) : 3810 - 3812
[4] Brown K, 2000, NAT STRUCT BIOL, V7, P191
[5] A robust palladium-catalyzed cyanation procedure: beneficial effect of zinc acetate
Chidambaram, R
[J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1441 - 1444
[6] A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides
Chobanian, HR
Fors, BP
Lin, LS
[J]. TETRAHEDRON LETTERS, 2006, 47 (19) : 3303 - 3305
[7] Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides
Cristau, HJ
Ouali, A
Spindler, JF
Taillefer, M
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2483 - 2492
[8] CYANATION OF AROMATIC HALIDES
ELLIS, GP
ROMNEYALEXANDER, TM
[J]. CHEMICAL REVIEWS, 1987, 87 (04) : 779 - 794
[9] Acidity of a Cu-bound histidine in the binuclear center of cytochrome C oxidase
Fadda, E
Chakrabarti, N
Pomès, R
[J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (47) : 22629 - 22640
[10] Grundmann C., 1985, METHODEN ORG CHEM E, VE5, P1313

← 1 2 3 4 5 →