Organocatalysis through halogen-bond activation

被引:226
作者
Bruckmann, Angelika [1 ]
Pena, Miguel A. [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
amine synthesis; halogen bonding; imine reduction; organocatalysis; quinoline reduction;
D O I
10.1055/s-2008-1042935
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Haloperfluoroalkanes have been used as catalysts for the reduction of 2-phenylquinoline to its corresponding 1,2,3,4-tetrahydro derivative using a Hantzsch ester as reductand. The results suggest a substrate activation by halogen bonding.
引用
收藏
页码:900 / 902
页数:3
相关论文
共 51 条
[1]   Structural competition between hydrogen bonds and halogen bonds [J].
Aakeroey, Christer B. ;
Fasulo, Meg ;
Schultheiss, Nate ;
Desper, John ;
Moore, Curtis .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13772-+
[2]   Crystal structures of two potent nonamidine inhibitors bound to factor Xa [J].
Adler, M ;
Kochanny, MJ ;
Ye, B ;
Rumennik, G ;
Light, DR ;
Biancalana, S ;
Whitlow, M .
BIOCHEMISTRY, 2002, 41 (52) :15514-15523
[3]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[4]   Perfluorocarbon-hydrocarbon self-assembling.: 1D infinite chain formation driven by nitrogen•••iodine interactions [J].
Amico, V ;
Meille, SV ;
Corradi, E ;
Mesina, MT ;
Resnati, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8261-8262
[5]  
[Anonymous], 2006, ANGEW CHEM, V118, P1550
[6]   Halogen bonds in biological molecules [J].
Auffinger, P ;
Hays, FA ;
Westhof, E ;
Ho, PS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (48) :16789-16794
[7]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8]   Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].
Bolm, C ;
Rantanen, T ;
Schiffers, I ;
Zani, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763
[9]  
Bolm C, 2005, ANGEW CHEM, V117, P1788
[10]   Self-assembly of nitroxide radicals via halogen bonding -: directional NO•...;I interactions [J].
Boubekeur, K ;
Syssa-Magalé, JL ;
Palvadeau, P ;
Schöllhorn, B .
TETRAHEDRON LETTERS, 2006, 47 (08) :1249-1252