A Well-Defined Aluminum-Based Lewis Acid as an Effective Catalyst for Diels-Alder Transformations

被引：15

作者：

Liu, Zhizhou ^{[1
]}

Lee, Jazreen Hui Qi ^{[1
]}

Ganguly, Rakesh ^{[1
]}

Vidovic, Dragoslav ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Dept Chem & Biol Chem, Singapore 637371, Singapore

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 32期

关键词：

aluminum; homogeneous catalysis; Diels-Alder reaction; Lewis acids; triflate; TRIHALIDE-TETRAHYDROFURAN COMPLEXES; MICHAEL ADDITION-REACTIONS; TRIFLIC ACID; SILYLIUM ION; TRIFLUOROMETHANESULFONATE; HYDROAMINATION; DICATION; ALCOHOLS; CHLORIDE; BROMIDE;

D O I：

10.1002/chem.201502205

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytically active aluminum-based system for Diels-Alder transformations is reported. The system was generated by mixing a -diketiminate-stabilized aluminum bistriflate compound with Na[BAr4Cl] (Ar-Cl=3,5-Cl2C6H3). Solid-state analysis of the catalytic system reveals a unique structure incorporating a two-dimensional coordination polymer. According to the experimental results obtained from several Diels-Alder transformations, the aluminum-based system appears to be a more practical and more robust alternative to the recently reported compounds based on carbon and silicon cations.

引用

页码：11344 / 11348

页数：5

共 45 条

[1] Carbocations as Lewis Acid Catalysts in Diels-Alder and Michael Addition Reactions
Bah, Juho
Franzen, Johan
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (04) : 1066 - 1072
[2] Budzelaar PHM, 2000, EUR J INORG CHEM, P753
[3] Cazeau P., 1978, TETRAHEDRON, V34, P2089
[4] Boron and aluminum complexes of sterically demanding phosphinimines and phosphinimides
Courtenay, Silke
Walsh, Denise
Hawkeswood, Sarah
Wei, Pingrong
Das, Anjan Kumar
Stephan, Douglas W.
[J]. INORGANIC CHEMISTRY, 2007, 46 (09) : 3623 - 3631
[5] CRYSTAL AND MOLECULAR-STRUCTURE OF THE 1-2 ALUMINUM TRICHLORIDE-TETRAHYDROFURAN COMPLEX ALCL3.2THF
COWLEY, AH
CUSHNER, MC
DAVIS, RE
RILEY, PE
[J]. INORGANIC CHEMISTRY, 1981, 20 (04) : 1179 - 1181
[6] SPECTROSCOPIC INVESTIGATION OF ALUMINUM TRIHALIDE-TETRAHYDROFURAN COMPLEXES .2. SOLUTIONS OF ALUMINUM-CHLORIDE OR BROMIDE IN TETRAHYDROFURAN AND IN TETRAHYDROFURAN-DICHLOROMETHANE
DEROUAULT, J
GRANGER, P
FOREL, MT
[J]. INORGANIC CHEMISTRY, 1977, 16 (12) : 3214 - 3218
[7] SPECTROSCOPIC INVESTIGATION OF ALUMINUM TRIHALIDE-TETRAHYDROFURAN COMPLEXES .1. STRUCTURE AND FORCE-FIELDS OF 1-1 AND 1-2 SOLID COMPOUNDS FORMED BY ALUMINUM-CHLORIDE OR BROMIDE
DEROUAULT, J
FOREL, MT
[J]. INORGANIC CHEMISTRY, 1977, 16 (12) : 3207 - 3213
[8] On the role of triflic acid in the metal triflate-catalysed acylation of alcohols
Dumeunier, R
Markó, IE
[J]. TETRAHEDRON LETTERS, 2004, 45 (04) : 825 - 829
[9] Fringuelli F., 2002, The Diels-Alder Reaction: Selected Practical Methods
[10] [AlCl3+2THF]:: A new and efficient catalytic system for Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions
Fringuelli, Francesco
Girotti, Rugiada
Pizzo, Ferdinando
Vaccaro, Luigi
[J]. ORGANIC LETTERS, 2006, 8 (12) : 2487 - 2489

← 1 2 3 4 5 →