scholarly journals Vinylogous and Arylogous Stereoselective Base-Promoted Phase-Transfer Catalysis

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1545
Author(s):  
Assunta D’Amato ◽  
Giorgio Della Sala

Vinylogous enolate and enolate-type carbanions, generated by deprotonation of α,β-unsaturated compounds and characterized by delocalization of the negative charge over two or more carbon atoms, are extensively used in organic synthesis, enabling functionalization and C–C bond formation at remote positions. Similarly, reactions with electrophiles at benzylic and heterobenzylic position are performed through generation of arylogous and heteroarylogous enolate-type nucleophiles. Although widely exploited in metal-catalysis and organocatalysis, it is only in recent years that the vinylogy and arylogy principles have been translated fruitfully in phase-transfer catalyzed processes. This review provides an overview of the methods developed to date, involving vinylogous and (hetero)arylogous carbon nucleophiles under phase-transfer catalytic conditions, highlighting main mechanistic aspects.

Catalysts ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 244 ◽  
Author(s):  
Hongyu Wang

Asymmetric phase-transfer catalysis has been widely applied into organic synthesis for efficiently creating chiral functional molecules. In the past decades, chiral phase-transfer catalysts with proton donating groups are emerging as an extremely significant strategy in the design of novel catalysts, and a large number of enantioselective reactions have been developed. In particular, the proton donating groups including phenol, amide, and (thio)-urea exhibited unique properties for cooperating with the phase-transfer catalysts, and great advances on this field have been made in the past few years. This review summarizes the seminal works on the design, synthesis, and applications of chiral phase-transfer catalysts with strong hydrogen bonding interactions.


1999 ◽  
Vol 150 (1-2) ◽  
pp. 113-131 ◽  
Author(s):  
Domenico Albanese ◽  
Dario Landini ◽  
Angelamaria Maia ◽  
Michele Penso

2014 ◽  
Vol 2014 ◽  
pp. 1-47 ◽  
Author(s):  
Ahmed M. El-Sayed ◽  
Omyma A. Abd Allah ◽  
Ahmed M. M. El-Saghier ◽  
Shaaban K. Mohamed

Phase transfer catalysts (PTCs) have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings.


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