A Stimuli-Responsive Rotaxane-Gold Catalyst: Regulation of Activity and Diastereoselectivity

被引:118
作者
Galli, Marzia [1 ]
Lewis, James E. M. [1 ]
Goldup, Stephen M. [1 ]
机构
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
基金
英国工程与自然科学研究理事会;
关键词
catalysts; gold; molecular machines; rotaxanes; supramolecular chemistry; MOLECULAR MACHINES; SWITCHABLE ORGANOCATALYST; TERMINAL ALKYNES; LIGANDS; CYCLOPROPANATION; ACTIVATION; CATENANES; HYDROALKOXYLATION; PHOSPHINE; CHEMISTRY;
D O I
10.1002/anie.201505464
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rotaxane-based Au catalyst was developed and the effect of the mechanical bond on its behavior was studied. Unlike the non-interlocked thread, the rotaxane requires a catalytically innocent cofactor, the identity of which significantly influences both the yield and diastereoselectivity of the reaction. Under optimized conditions, Au-I (the catalyst), Ag-I (to abstract the Cl- ligand), and Cu-I (the cofactor) combine to produce a catalyst with excellent activity and selectivity.
引用
收藏
页码:13545 / 13549
页数:5
相关论文
共 81 条
[1]   Encapsulation Studies of Cationic Gold Complexes within a Self-Assembled Hexameric Resorcin[4]arene Capsule [J].
Adriaenssens, Louis ;
Escribano-Cuesta, Ana ;
Homs, Anna ;
Echavarren, Antonio M. ;
Ballester, Pablo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (08) :1494-1500
[2]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[3]  
Altenhoff G., 2003, Angew. Chem, V115, P3818, DOI [10.1002/ange.200351325, DOI 10.1002/ANGE.200351325]
[4]  
[Anonymous], 2013, ANGEW CHEM
[5]  
[Anonymous], 2015, ANGEW CHEM
[6]  
[Anonymous], 2011, ANGEW CHEM-GER EDIT
[7]   Squaraine-derived rotaxanes: Sterically protected fluorescent near-IR dyes [J].
Arunkumar, E ;
Forbes, CC ;
Noll, BC ;
Smith, BD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3288-3289
[8]   Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures [J].
Aucagne, V ;
Hänni, KD ;
Leigh, DA ;
Lusby, PJ ;
Walker, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2186-2187
[9]   Synthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of Vinyl Arenes and in Intramolecular Hydroalkoxylation of Allenes [J].
Bartolome, Camino ;
Garcia-Cuadrado, Domingo ;
Ramiro, Zoraida ;
Espinet, Pablo .
INORGANIC CHEMISTRY, 2010, 49 (21) :9758-9764
[10]   Azodicarboxamides as Template Binding Motifs for the Building of Hydrogen-Bonded Molecular Shuttles [J].
Berna, Jose ;
Alajarin, Mateo ;
Orenes, Raul-Angel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) :10741-10747