Nickel(0)/imidazolium chloride catalyzed reduction of aryl halides

被引:134
作者
Desmarets, C [1 ]
Kuhl, S [1 ]
Schneider, R [1 ]
Fort, Y [1 ]
机构
[1] Univ Henri Poincare, UMR 7565, Fac Sci, F-54506 Vandoeuvre Les Nancy, France
关键词
D O I
10.1021/om010949+
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Dehalogenation of aryl halides was efficiently performed in refluxing THF using a catalytic combination composed of Ni(0)/N-heterocyclic carbene (NHC)/beta-hydrogen-containing alkoxide. 1Mes.HCl (1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride) and Ni(acac)2 used respectively as carbene and Ni(0) precursors associated to in situ generated i-PrONa were found to be the most effective for the dehalogenation of functionalized aryl chlorides, bromides, iodides, and polyhalogenated hydrocarbons.
引用
收藏
页码:1554 / 1559
页数:6
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共 83 条
[71]   Unexpected reactivity of two-coordinate palladium-carbene complexes; synthetic and catalytic implications [J].
Titcomb, LR ;
Caddick, S ;
Cloke, FGN ;
Wilson, DJ ;
McKerrecher, D .
CHEMICAL COMMUNICATIONS, 2001, (15) :1388-1389
[72]   Hydrogen-transfer hydrodehalogenation of aromatic halides with alcohols in the presence of noble metal catalysts [J].
Ukisu, Y ;
Miyadera, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 125 (2-3) :135-142
[73]   ACTIVATION OF REDUCING AGENTS - SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS .15. REDUCTION AND SELECTIVE REDUCTION OF ORGANIC HALIDES [J].
VANDERESSE, R ;
BRUNET, JJ ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1270-1277
[74]   Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system [J].
Viciu, MS ;
Grasa, GA ;
Nolan, SP .
ORGANOMETALLICS, 2001, 20 (16) :3607-3612
[75]   Room-temperature hydrodebromination of 4,4′-dibromobiphenyl catalyzed by 1,1′-bis(diphenylphosphino) ferrocene complexes of palladium [J].
Wei, B ;
Hor, TSA .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 132 (2-3) :223-229
[76]   Liquid phase catalytic hydrodechlorination of chlorobenzene over supported nickel and palladium catalysts: an NMR insight into solvent function [J].
Yakovlev, VA ;
Terskikh, VV ;
Simagina, VI ;
Likholobov, VA .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 153 (1-2) :231-236
[77]   Rapid and complete hydrodechlorination of 2,4-dichlorophenoxyacetic acid catalyzed by Pd/TiO2 with H2 in deionized water [J].
Yamanaka, I ;
Nishikawa, K ;
Otsuka, K .
CHEMISTRY LETTERS, 2001, (04) :368-369
[78]   Hydrodefluorination of fluorobenzene and 1,2-difluorobenzene under mild conditions over rhodium pyridylphosphine and bipyridyl complexes tethered on a silica-supported palladium catalyst [J].
Yang, H ;
Gao, HR ;
Angelici, RJ .
ORGANOMETALLICS, 1999, 18 (12) :2285-2287
[79]   Catalytic C-F bond activation of nonactivated monofluoroarenes [J].
Young, RJ ;
Grushin, VV .
ORGANOMETALLICS, 1999, 18 (03) :294-296
[80]   PALLADIUM HYDRIDES IN ORGANIC-SYNTHESIS - REDUCTION OF ARYL HALIDES BY SODIUM METHOXIDE CATALYZED BY TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM [J].
ZASK, A ;
HELQUIST, P .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1619-1620