Practical Imidazole-Based Phosphine Ligands for Selective Palladium-Catalyzed Hydroxylation of Aryl Halides

被引:220
作者
Schulz, Thomas [1 ]
Torborg, Christian [1 ]
Schaeffner, Benjamin [1 ]
Huang, Jun [1 ]
Zapf, Alexander [1 ]
Kadyrov, Renat [2 ]
Boerner, Armin [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[2] Evonik Dugussa GmbH, Business Line Catalysis, D-63457 Hanau, Germany
关键词
chemoselectivity; homogeneous catalysis; hydroxylation; palladium; phosphines; N BOND FORMATION; ALPHA-ARYLATION; GENERAL-METHOD; C-N; COUPLING REACTIONS; CROSS-COUPLINGS; AMINATION; CHLORIDES; ESTERS; ETHERS;
D O I
10.1002/anie.200804898
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The phenol countdown: Novel imidazole-based phosphine ligands are synthesized on scales up to 100 g by a convenient lithiation-phosphorylation method. The phosphines are stable towards air and moisture and are successfully applied as ligands in the palladium-catalyzed selective hydroxylation of aryl halides (see scheme, dba=dibenzylideneacetone). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:918 / 921
页数:4
相关论文
共 73 条
[1]   Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions [J].
Alcalde, E ;
Dinarès, I ;
Rodríguez, S ;
de Miguel, CG .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1637-1643
[2]   THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II) [J].
ALLEN, DW ;
TAYLOR, BF .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01) :51-54
[3]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[4]  
[Anonymous], 2006, ANGEW CHEM
[5]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[6]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[7]   Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands [J].
Beare, NA ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :541-555
[8]  
Beller M., 2004, SPEC CHEM, V24, P22
[9]  
Burgos C. H., 2006, ANGEW CHEM, V118, P4427
[10]   Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].
Burgos, Carlos H. ;
Barder, Timothy E. ;
Huang, Xiaohua ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326