Tandem Regioselective Hydroformylation-Hydrogenation of Internal Alkynes Using a Supramolecular Catalyst

被引:29
作者
Fang, Weiwei [1 ]
Breit, Bernhard [1 ]
机构
[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, Freiburg, Germany
关键词
alkynes; hydroformylation; ligand design; rhodium; supramolecular chemistry; COMBINATORIAL HOMOGENEOUS CATALYSIS; ZWITTERIONIC RHODIUM COMPLEX; BIDENTATE LIGANDS; DECARBOXYLATIVE HYDROFORMYLATION; NONCOVALENT INTERACTIONS; SELECTIVITY; OXYGENATION; LACTONE; ARENES; MH-031;
D O I
10.1002/anie.201809073
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New supramolecular ligands containing an acyl guanidine function were designed based on the strategy of increasing the -acceptor ability of phosphine ligands by introducing electron-withdrawing groups. By applying this novel catalytic system, a general protocol for the Rh-catalysed hydroformylation-hydrogenation of unsymmetrical internal alkynes, functionalized with a carboxylic acid, was found to furnish aliphatic aldehydes in high regio- and chemoselectivities. Control experiments confirm the enzyme-like supramolecular catalyst mode of action.
引用
收藏
页码:14817 / 14821
页数:5
相关论文
共 58 条
[1]   Rhodium-catalyzed hydroformylation of alkynes employing a self-assembling ligand system [J].
Agabekov, Vladislav ;
Seiche, Wolfgang ;
Breit, Bernhard .
CHEMICAL SCIENCE, 2013, 4 (06) :2418-2422
[2]  
[Anonymous], 2013, ANGEW CHEM
[3]  
[Anonymous], 2007, ANGEW CHEM
[4]  
[Anonymous], 2008, ANGEW CHEM
[5]   Supramolecular approaches to generate libraries of chelating bidentate ligands for homogeneous catalysis [J].
Breit, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6816-6825
[6]   Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base-pair model [J].
Breit, B ;
Seiche, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1640-1643
[7]   Hydrogen bonding as a construction element for bidentate donor ligands in homogeneous catalysis: Regioselective hydroformylation of terminal alkenes [J].
Breit, B ;
Seiche, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6608-6609
[8]  
Breit B., 2005, Angew. Chem, V117, P1666
[9]  
Breit B., 2005, Angew. Chem, V117, P6976
[10]   Ground state and transition state contributions to the rates of intramolecular and enzymatic reactions [J].
Bruice, TC ;
Lightstone, FC .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (02) :127-136