Routes to fluorinated organic derivatives by nickel mediated C-F activation of heteroaromatics

被引:205
作者
Braun, T
Perutz, RN
机构
[1] Univ Bielefeld, Fak Chem, D-33501 Bielefeld, Germany
[2] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1039/b206154f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New fluorinated azaheterocycles can be synthesised regio- and chemo-selectively via C-F activation of fluorinated precursors at nickel, with subsequent functionalisation and release from the coordination sphere of the metal; the requirements for productive C- F activation are significantly different from those for C-H bond activation.
引用
收藏
页码:2749 / 2757
页数:9
相关论文
共 82 条
[1]   Reaction of metal diethylnitroxides with pentafluoropyridine, pentafluorobenzene, octafluorotoluene and 2-chloro-3- or 5-nitropyridine [J].
Adamson, AJ ;
Jondi, WJ ;
Tipping, AE .
JOURNAL OF FLUORINE CHEMISTRY, 1996, 76 (01) :67-78
[2]   HOMOGENEOUS METAL-CATALYZED HYDROGENOLYSIS OF C-F BONDS [J].
AIZENBERG, M ;
MILSTEIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) :8674-8675
[3]   CATALYTIC ACTIVATION OF CARBON-FLUORINE BONDS BY A SOLUBLE TRANSITION-METAL COMPLEX [J].
AIZENBERG, M ;
MILSTEIN, D .
SCIENCE, 1994, 265 (5170) :359-361
[4]   Chemistry of nickel tetrafluoropyridyl derivatives:: their versatile behaviour with Bronsted acids and the Lewis acid BF3 [J].
Archibald, SJ ;
Braun, T ;
Gaunt, JA ;
Hobson, JE ;
Perutz, RN .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (13) :2013-2018
[5]   Synthesis, structure, and properties of {((t)Bu(2)PC(2)H(4)P(t)Bu(2))Ni}(2)(mu-eta(2):eta(2)-C6H6) and ((t)Bu(2)PC(2)H(4)P(t)Bu(2))Ni(eta(2)-C6F6) [J].
Bach, I ;
Porschke, KR ;
Goddard, R ;
Kopiske, C ;
Kruger, C ;
Rufinska, A ;
Seevogel, K .
ORGANOMETALLICS, 1996, 15 (23) :4959-4966
[6]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[7]  
Beletskaya IP, 1996, J PHYS ORG CHEM, V9, P319, DOI 10.1002/(SICI)1099-1395(199606)9:6<319::AID-POC786>3.0.CO
[8]  
2-7
[9]   ETA(2)-COORDINATION AND C-F ACTIVATION OF HEXAFLUOROBENZENE BY CYCLOPENTADIENYLRHODIUM AND CYCLOPENTADIENYLIRIDIUM COMPLEXES [J].
BELT, ST ;
HELLIWELL, M ;
JONES, WD ;
PARTRIDGE, MG ;
PERUTZ, RN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1429-1440
[10]   Multi-substituted heterocycles [J].
Benmansour, H ;
Chambers, RD ;
Hoskin, PR ;
Sandford, G .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (01) :133-137