Phase-Transfer and Other Types of Catalysis with Cyclopropenium Ions

被引:49
作者
Bandar, Jeffrey S. [1 ]
Tanaset, Anont [1 ]
Lambert, Tristan H. [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
aromaticity; aromatic ions; cyclopropenium; phase-transfer catalysis; structure-activity relationships; QUATERNARY AMMONIUM-IONS; INTERFACIAL-CATALYSIS; DRIVING-FORCE; PAIR STRAIN; IODIDE-IONS; CATIONS; SALTS; BIS(AMINO)CYCLOPROPENYLIDENES; TETRACHLOROCYCLOPROPENE; TRICATIONS;
D O I
10.1002/chem.201500124
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This work establishes the cyclopropenium ion as a viable platform for efficient phase-transfer catalysis of a diverse range of organic transformations. The amenability of these catalysts to large-scale synthesis and structural modification is demonstrated. Evaluation of the molecular structure of an optimal catalyst reveals some unique structural features of these systems. Finally, a discussion of electronic charge distribution underscores an important consideration for catalyst design.
引用
收藏
页码:7365 / 7368
页数:4
相关论文
共 63 条
[1]   Liquid-liquid phase transfer catalysis:: Basic principles and synthetic applications (Reprinted from Interfacial Catalysis, pg 203-226, 2003) [J].
Albanese, D .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2003, 45 (3-4) :369-395
[2]  
[Anonymous], 2011, ANGEW CHEM-GER EDIT
[3]   Aminocyclopropenium Ions: Synthesis, Properties, and Applications [J].
Bandar, Jeffrey S. ;
Lambert, Tristan H. .
SYNTHESIS-STUTTGART, 2013, 45 (18) :2485-2498
[4]   Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines [J].
Bandar, Jeffrey S. ;
Lambert, Tristan H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5552-5555
[5]  
Bruns H., 2010, ANGEW CHEM, V122, P3762
[6]   Synthesis and Coordination Properties of Nitrogen(I)-Based Ligands [J].
Bruns, Hans ;
Patil, Mahendra ;
Carreras, Javier ;
Vazquez, Arcadio ;
Thiel, Walter ;
Goddard, Richard ;
Alcarazo, Manuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (21) :3680-3683
[7]  
Butchard J. R., 2006, ANGEW CHEM, V118, P7712
[8]   Structural and spectroscopic investigations of non-planar tris(dialkylamino)cyclopropenium cations [J].
Butchard, James R. ;
Curnow, Owen J. ;
Pipal, Robert J. ;
Robinson, Ward T. ;
Shang, Rong .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2008, 21 (02) :127-135
[9]   Structure of a discrete dichloride hexahydrate cube as a tris(diisopropylamino)cyclopropenium salt [J].
Butchard, James R. ;
Curnow, Owen J. ;
Garrett, David J. ;
Maclagan, Robert G. A. R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7550-7553
[10]   Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L3P] 3+: Applications in Pt(II) Catalysis [J].
Carreras, Javier ;
Patil, Mahendra ;
Thiel, Walter ;
Alcarazo, Manuel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) :16753-16758