Design and Applications of Phase Transfer Catalysis

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (10 February 2022) | Viewed by 5588

Special Issue Editors


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Guest Editor
Dipartimento di Chimica e Biologia "Adolfo Zambelli" DCB, Università di Salerno, Salerno, Italy
Interests: stereoselective organocatalyzed and metal-catalyzed reactions; enantioselective synthesis; phase–transfer catalysis; macrocyclic catalysts; synthesis and applications of cyclic peptoids
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Department of Chemistry and Biology "Adolfo Zambelli" DCB, University of Salerno, Fisciano, Italy
Interests: synthesis and biological applications of peptidomimetics; organometallic complexes synthesis, catalytical, and biological applications; stereoselective catalysis; biomaterials chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since its first introduction, in the late 1960s, phase transfer catalysis (PTC) has continued to expand its applications in laboratory and industrial processes over the decades. The reasons for this great popularity can be traced back to the operational simplicity and environmental sustainability of this methodology. In fact, PTC combines increased reaction rates in heterogeneous systems, high selectivity, and mild reaction conditions with the employment of non-toxic and recyclable solvents and catalysts. Moreover, phase transfer base-mediated processes are typically conducted with aqueous or solid alkali metal salts such as hydroxides, carbonates or phosphates (PTC/OH conditions), avoiding moisture-sensitive reagents and strictly anhydrous conditions. Today, a considerable number of organic reactions have been developed under phase transfer conditions, typically promoted by quaternary ammonium and phosphonium salts, crown ethers, cryptands, and polyethers. The use of properly designed chiral onium salts and crown ethers is a well-established strategy to perform a wide range of enantioselective processes. However, the continuous effort in this field is leading to the development of newly designed catalysts, including triazolium, pentanidinium and 2-oxopyrimidinium salts, while other studies are focused on increasing the synthetic applications of this methodology.

This Special Issue aims to give space to all the recent advances and innovative applications of phase transfer catalysis both in academic and industrial areas. Research articles, short communications, brief reports, and review papers on this topic are welcome.

Prof. Dr. Giorgio Della Sala
Dr. Assunta D'Amato
Guest Editors

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Keywords

  • Phase-transfer catalysis
  • Ion pair catalysis
  • Heterogeneous catalysis
  • Organocatalysis
  • Quaternary ammonium salts
  • Quaternary phosphonium salts
  • Crown ethers
  • Industrial processes
  • Continuous flow processes
  • Supported catalysts
  • Green chemistry

Published Papers (2 papers)

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Research

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15 pages, 1619 KiB  
Article
Asymmetric Phase Transfer Catalysed Michael Addition of γ-Butenolide and N-Boc-Pyrrolidone to 4-Nitro-5-styrylisoxazoles
by Diana Salazar Illera, Roberta Pacifico and Mauro F. A. Adamo
Catalysts 2022, 12(6), 634; https://doi.org/10.3390/catal12060634 - 10 Jun 2022
Viewed by 1773
Abstract
Herein we report the addition of acidic γ-butenolide and N-Boc-pyrrolidone to 4-nitro-5-styrylisoxazoles, a popular class of cinnamic ester synthetic equivalent. The reactions proceeded under the catalysis of Cinchona-based phase-transfer catalysts. Functionalised γ-butenolides were obtained in good isolated yields and moderate enantioselectivity [...] Read more.
Herein we report the addition of acidic γ-butenolide and N-Boc-pyrrolidone to 4-nitro-5-styrylisoxazoles, a popular class of cinnamic ester synthetic equivalent. The reactions proceeded under the catalysis of Cinchona-based phase-transfer catalysts. Functionalised γ-butenolides were obtained in good isolated yields and moderate enantioselectivity (up to 74% ee). Full article
(This article belongs to the Special Issue Design and Applications of Phase Transfer Catalysis)
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Review

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41 pages, 24699 KiB  
Review
Vinylogous and Arylogous Stereoselective Base-Promoted Phase-Transfer Catalysis
by Assunta D’Amato and Giorgio Della Sala
Catalysts 2021, 11(12), 1545; https://doi.org/10.3390/catal11121545 - 18 Dec 2021
Cited by 4 | Viewed by 3020
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Design and Applications of Phase Transfer Catalysis)
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