Catalytic carbon-fluorine bond activation with monocoordinated nickel-carbene complexes: reduction of fluoroarenes

被引:101
作者
Kuhl, S [1 ]
Schneider, R [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, Lab Synth Organ & React, UMR CNRS UHP 7565, F-54506 Vandoeuvre Les Nancy, France
关键词
catalysis; fluoroarenes; nickel(O)/N-heterocyclic carbene complex; reduction;
D O I
10.1002/adsc.200390036
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Monocoordinate nickel/N-heterocyclic carbene complexes reveal unexpected reactivity towards aryl fluorides. Defluorination reactions were efficiently performed with a beta-hydrogen-containing alkoxide (3 equiv.) in the presence of 3 mol % of [1:1] Ni(O)/IMes . HCI catalyst (IMes = 1,3-dimesitylimidazol-2-ylidene).
引用
收藏
页码:341 / 344
页数:4
相关论文
共 35 条
[1]   HOMOGENEOUS METAL-CATALYZED HYDROGENOLYSIS OF C-F BONDS [J].
AIZENBERG, M ;
MILSTEIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) :8674-8675
[2]   CATALYTIC ACTIVATION OF CARBON-FLUORINE BONDS BY A SOLUBLE TRANSITION-METAL COMPLEX [J].
AIZENBERG, M ;
MILSTEIN, D .
SCIENCE, 1994, 265 (5170) :359-361
[3]   DIBENZO[A,E]CYCLOOCTATETRAENE IN A PROPOSED TEST FOR HETEROGENEITY IN CATALYSTS FORMED FROM SOLUBLE PLATINUM GROUP METAL-COMPLEXES [J].
ANTON, DR ;
CRABTREE, RH .
ORGANOMETALLICS, 1983, 2 (07) :855-859
[4]  
Arduengo A. J., 1991, U. S. Patent, Patent No. [5,077,414, 5077414]
[5]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[6]  
Böhm VPW, 2001, ANGEW CHEM INT EDIT, V40, P3387
[7]   Catalytic C-F activation of polyfluorinated pyridines by nickel-mediated cross-coupling reactions [J].
Braun, T ;
Perutz, RN ;
Sladek, MI .
CHEMICAL COMMUNICATIONS, 2001, (21) :2254-2255
[8]  
Braun T, 1999, ANGEW CHEM INT EDIT, V38, P3326, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3326::AID-ANIE3326>3.0.CO
[9]  
2-7
[10]   Recent advances in C-F bond activation [J].
Burdeniuc, J ;
Jedlicka, B ;
Crabtree, RH .
CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (02) :145-154