Formation of Acetals under Rhodium-Catalyzed Hydroformylation Conditions in Alcohols

被引:26
作者
Diebolt, Olivier [1 ]
Cruzeuil, Clement [1 ]
Muller, Christian [1 ]
Vogt, Dieter [1 ]
机构
[1] Eindhoven Univ Technol, Schuit Inst Catalysis, Lab Homogeneous Catalysis, NL-5600 MB Eindhoven, Netherlands
关键词
acetals; alcohols; alkenes; hydroformylation; phosphorus ligands; rhodium; TANDEM REACTION SEQUENCES; SELECTIVE HYDROAMINOMETHYLATION; ASYMMETRIC HYDROFORMYLATION; SYNTHETIC APPLICATIONS; BITE ANGLE; ALKENES; LIGANDS; ACETALIZATION; PHOSPHITE; OLEFINS;
D O I
10.1002/adsc.201100707
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Hydroformylation of terminal alkenes in alcohol solvents leads to the selective formation of the corresponding acetals. The Xantphos ligand gave the best results as well as acetal selectivities higher than 99% and linear/branched ratios of up to 52 were obtained. The scope of the reaction was studied. Acetals were found to be unreactive under hydroaminomethylation conditions.
引用
收藏
页码:670 / 677
页数:8
相关论文
共 49 条
[1]  
AHLERS W, 2002, Patent No. 2002083695
[2]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[3]  
[Anonymous], 1999, ANGEW CHEM
[4]   Hydroformylation of styrene catalyzed by a rhodium thiolate binuclear catalyst supported on a cationic exchange resin [J].
Balué, J ;
Bayón, JC .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 137 (1-3) :193-203
[5]   Phosphabarrelene-modified Rh-catalysts: a new and selective route towards hydroxy-functionalized bicyclic imidazoles via tandem reactions [J].
Bauerlein, Patrick S. ;
Gonzalez, Ismael Arenas ;
Weemers, Jarno J. M. ;
Lutz, Martin ;
Spek, Anthony L. ;
Vogt, Dieter ;
Muller, Christian .
CHEMICAL COMMUNICATIONS, 2009, (33) :4944-4946
[6]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[7]  
CASEY CP, 1990, ISRAEL J CHEM, V30, P299
[8]   Effect of the dihedral angle of biaryl-bridged bisphosphite ligands on enantioselectivity and regioselectivity of asymmetric hydroformylation [J].
Cobley, Christopher J. ;
Froese, Robert D. J. ;
Klosin, Jerzy ;
Qin, Cheng ;
Whiteker, Gregory T. ;
Abboud, Khalil A. .
ORGANOMETALLICS, 2007, 26 (12) :2986-2999
[9]  
Diab L., 2009, ANGEW CHEM, V121, P8166
[10]   Supramolecular Catalyst for Aldehyde Hydrogenation and Tandem Hydroformylation-Hydrogenation [J].
Diab, Lisa ;
Smejkal, Tomas ;
Geier, Jens ;
Breit, Bernhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8022-8026