Cobalt-Catalyzed 1,4-Hydrobutadienylation of 1-Aryl-1,3-dienes with 2,3-Dimethyl-1,3-butadiene

被引:39
作者
Bohn, Martin A. [1 ]
Schmidt, Anastasia [1 ]
Hilt, Gerhard [1 ]
Dindaroglu, Mehmet [2 ]
Schmalz, Hans-Guenther [2 ]
机构
[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
[2] Univ Cologne, Dept Chem, D-50939 Cologne, Germany
关键词
alkenes; cobalt; homogeneous catalysis; hydrobutadienylation; polyenes; PHOSPHINE-PHOSPHITE-LIGANDS; BIDENTATE CHELATE LIGANDS; ASYMMETRIC HYDROVINYLATION; BICYCLIC ALKENES; CYCLOADDITION; 1,3-DIENES; 1,4-HYDROVINYLATION; CYCLOTRIMERIZATION; HYDROFORMYLATION; 1,4-ADDITION;
D O I
10.1002/anie.201103613
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Round and round the olefin goes! A cobalt-catalyzed 1,4- hydrobutadienylation of a 1-aryl-substituted 1,3-diene with 2,3-dimethyl-1,3- butadiene yields 1,3,6-triene derivatives in excellent yield and chemoselectivity. The application of a bulky ligand (SchmalzPhos) leads to the selective formation of a single regio- and stereoisomer. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9689 / 9693
页数:5
相关论文
共 56 条
[1]   Cobalt-Catalyzed 1,4-Hydrovinylation of Allylsilane and Allylboronic Esters for the Synthesis of Hydroxy-Functionalized 1,4-Dienes [J].
Arndt, Marion ;
Reinhold, Anne ;
Hilt, Gerhard .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5203-5210
[2]   An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides [J].
Battistuzzi, G ;
Cacchi, S ;
Fabrizi, G .
ORGANIC LETTERS, 2003, 5 (05) :777-780
[3]  
Blume F, 2002, ADV SYNTH CATAL, V344, P868, DOI 10.1002/1615-4169(200209)344:8<868::AID-ADSC868>3.0.CO
[4]  
2-M
[5]  
Buisine O, 2001, CHEM-EUR J, V7, P3517, DOI 10.1002/1521-3765(20010817)7:16<3517::AID-CHEM3517>3.0.CO
[6]  
2-V
[7]   Ruthenium-Catalyzed [2+2] Cycloadditions of Bicyclic Alkenes with Alkynyl Phosphonates [J].
Cockburn, Neil ;
Karimi, Elham ;
Tam, William .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5762-5765
[8]   Regioselective Cobalt-Catalyzed Formation of Bicyclic 3-and 4-Aminopyridines [J].
Garcia, Pierre ;
Evanno, Yannick ;
George, Pascal ;
Sevrin, Mireille ;
Ricci, Gino ;
Malacria, Max ;
Aubert, Corinne ;
Gandon, Vincent .
ORGANIC LETTERS, 2011, 13 (08) :2030-2033
[9]   Highly selective cobalt-catalyzed hydrovinylation of styrene [J].
Grutters, Michiel M. P. ;
Muller, Christian ;
Vogt, Dieter .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7414-7415
[10]   Asymmetric Synthesis of Axially Chiral 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2+2+2] Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitrites [J].
Hapke, Marko ;
Kral, Karolin ;
Fischer, Christine ;
Spannenberg, Anke ;
Gutnov, Andrey ;
Redkin, Dmitry ;
Heller, Barbara .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :3993-4003