A Green and Efficient Synthesis of 9-Aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using a Task-Specific Ionic Liquid as Dual Catalyst and Solvent

2007 ◽  
Vol 60 (2) ◽  
pp. 146 ◽  
Author(s):  
Jingjun Ma ◽  
Xin Zhou ◽  
Xiaohuan Zang ◽  
Chun Wang ◽  
Zhi Wang ◽  
...  

A green and efficient method for the preparation of 9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione has been developed using functionalized ionic liquids as a catalyst and a reaction medium. The nature of both the counter anion and cation influence the catalytic performance of the ionic liquids. The ionic liquid can be recycled and reused without apparently loss of activity.

2019 ◽  
Vol 16 (7) ◽  
pp. 550-555
Author(s):  
Dinesh K. Jangid ◽  
Keshav L. Ameta ◽  
Surbhi Dhadda ◽  
Anjali Guleria ◽  
Prakash G. Goswami ◽  
...  

Ionic Liquid assisted efficient synthesis of some 2-aminobenzenethiols has been reported using three different Ionic Liquids (ILs) namely methylimidazolium tetrafluoroborate [MIM]+[BF4]−, methylimidazolium chloride [MIM]+[Cl]− and methylimidazolium nitrate [MIM]+[NO3]−. A comparative study has been carried out for the synthesis of target molecules in the presence and absence of IL, leading to conclusion that maximum yield has been observed with [MIM]+[BF4]−.


ChemInform ◽  
2005 ◽  
Vol 36 (41) ◽  
Author(s):  
Zhang-Gao Le ◽  
Zhen-Chu Chen ◽  
Yi Hu ◽  
Qin-Guo Zheng

2021 ◽  
Vol 08 ◽  
Author(s):  
Vivek Srivastava

Background: Baylis-Hillman reaction suffers from the requirement of cheap starting materials, easy reaction protocol, possibility to create the chiral center in the reaction product has increased the synthetic efficacy of this reaction, and high catalyst loading, low reaction rate, and poor yield. Objective: The extensive use of various functional or non-functional ionic liquids (ILs) with organocatalyst increases the reaction rate of various organic transformations as a reaction medium and as a support to anchor the catalysts. Methods: In this manuscript, we have demonstrated the synthesis of quinuclidine-supported trimethylamine-based functionalized ionic liquid as a catalyst for the Baylis-Hillman reaction. Results: We obtained the Baylis-Hillman adducts in good, isolated yield, low catalyst loading, short reaction time, broad substrate scope, accessible product, and catalyst recycling. N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide was also successfully synthesized using CATALYST-3 promoted Baylis-Hillman reaction. Conclusion: We successfully isolated the 25 types of Baylis-Hillman adducts using three different quinuclidine-supported ammonium-based ionic liquids such as Et3AmQ][BF4] (CATALYST-1), [Et3AmQ][PF6] (CATALYST-2), and [TMAAmEQ][NTf2](CATALYST-3) as new and efficient catalysts. Tedious and highly active N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide derivative was also synthesized using CATALYST-3 followed by Baylis-Hillman reaction. Generally, all the responses demonstrated higher activity and yielded high competition with various previously reported homogenous and heterogeneous Catalytic systems. Easy catalyst and product recovery followed by six catalysts recycling were the added advantages of the prosed catalytic system.


2017 ◽  
Vol 7 (10) ◽  
pp. 2065-2073 ◽  
Author(s):  
Jie Deng ◽  
Bao-Hua Xu ◽  
Yao-Feng Wang ◽  
Xian-En Mo ◽  
Rui Zhang ◽  
...  

A highly efficient synthesis of isosorbide from sorbitol was developed using Brønsted acidic ionic liquids (BILs) as the catalyst for the first time.


2021 ◽  
Author(s):  
Guiling Shi ◽  
Ran Zhai ◽  
Haoran Li ◽  
Congmin Wang

A dual functionalized ionic liquid catalytic system was developed for the reaction between CO2 and propargylic alcohols, and exhibited excellent performance and good reusability, even under a low concentration of CO2 in a gram-scale reaction.


2007 ◽  
Vol 79 (11) ◽  
pp. 1869-1877 ◽  
Author(s):  
Anthony E. Rosamilia ◽  
Christopher R. Strauss ◽  
Janet L. Scott

Adducts of dimethylamine and carbon dioxide form a "distillable ionic liquid" (DIMCARB) that may used as both a reaction medium and catalyst in the direct, atom-economical synthesis of useful synthetic building blocks, such as mono-condensed α,β-unsaturated ketones. The utilization of such building blocks in the synthesis of two new classes of versatile macrocycles, by a sequence of condensation reactions (H2O by-product), is described. Investigation into the mechanism of action of DIMCARB catalysis and observation of an aniline impurity arising from a competing reaction sequence led to development of a new multicomponent reaction for the direct preparation of 2- or 4-substituted anilines. Some of the macrocycles and anilines are, respectively, supramolecular host compounds and ligands for the preparation of metal complexes.


2010 ◽  
Vol 88 (1) ◽  
pp. 27-34 ◽  
Author(s):  
Jocelyn J. Tindale ◽  
Paul J. Ragogna

An ionic liquid, covalently tethered to an efficient transition-metal catalyst in the presence of an ionic liquid reaction medium, can utilize ionophilic interactions to improve catalyst activity, recyclability, and product isolation while decreasing catalyst leaching. Given the greater stability of phosphonium salts in comparison to imidazolium ionic liquids under basic conditions, phosphonium-tagged oxime carbopalladacycle salts were prepared and employed in both Heck and Suzuki–Miyaura reactions. The desired product was obtained in good yields for up to four catalyst cycles in the case of the Suzuki–Miyaura reaction. While taking advantage of the non-volatile nature of ionic liquids, the product was isolated through simple sublimation from the reaction mixture, eliminating issues associated with catalyst leaching, and the remaining ionic liquid solvent–catalyst mixture was ready for further catalysis.


2011 ◽  
Vol 64 (12) ◽  
pp. 1624 ◽  
Author(s):  
Shahana A. Chowdhury ◽  
Pamela M. Dean ◽  
R. Vijayaraghavan ◽  
D. R. MacFarlane

A direct, one pot synthesis of an ellagic acid salt was achieved at room temperature by dimerization of ethyl gallate using N,N-dimethylammonium N′,N′-dimethylcarbamate, a distillable ionic liquid, as solvent.


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