Exploring Hydrogen Bond and Bronsted Acid Catalysis

A special issue of Catalysts (ISSN 2073-4344).

Deadline for manuscript submissions: closed (15 December 2019) | Viewed by 4144

Special Issue Editor


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Guest Editor
Brock University, Department of Chemistry, St Catharines, Canada
Interests: organo- and transition metal catalysis, organic chemistry, cyclopropenium and cyclopropenimine catalysis and applications, DFT calculations, hydrogen bond catalysis, mechanisms, fluorescencent compounds synthesis

Special Issue Information

Dear Colleagues,

The field of catalysis continues to evolve towards sustainable and renewable modes of reactivity, less reliant on precious metals, superseded by small molecule, viz., organocatalytic methodologies. The impetus for this shift being the intrinsic non-metal feature of organocatalysis, functional group tolerance and the involvement of multiple attractive noncovalent interactions in such processes. In this context, over the last two decades, hydrogen bond and Brønsted acid organocatalyzed approaches have emerged as promising subsets of catalysis and as such, they continue to receive tremendous attention from research groups. The basis for this being the proven high efficiency and versatility of these modes of catalysis for an ever-expanding list of synthetic transformations. Further hydrogen bond and Brønsted acid catalyzed protocols generally provide chemo-, regio- and stereoselectivity under mild conditions, thereby avoiding the production of by-products. 

Inherit mechanistic differences between Brønsted acid catalysis and hydrogen bond catalysis, however, are not always simple to delineate experimentally. The distinction between the two, broadly speaking, being Brønsted acid catalysis involves protonated ion pairs, while hydrogen bond catalysis involves hydrogen bond complexes. This divergent character while often overlooked, nevertheless, is paramount to mechanistic understanding. Computational studies provide an ideal means for differentiating between these two activation modes. 

Submissions to this special issue entitled “Exploring Hydrogen Bond and Brønsted Acid Catalysis” are welcome in the form of original research papers or short reviews that reflect the state of research in hydrogen bond catalysis and Brønsted acid catalysis. This includes computational, kinetic and/or experimental focused contributions.

Prof. Dr. Travis Dudding
Guest Editor

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Keywords

  • Hydrogen Bond Catalysis
  • Brønsted Acid Catalysis
  • Computational Studies
  • DFT Calculations
  • Ion Pairs
  • Organocatalysis

Published Papers (1 paper)

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Research

14 pages, 1620 KiB  
Article
Synergistic Palladium-Phosphoric Acid Catalysis in (3 + 2) Cycloaddition Reactions between Vinylcyclopropanes and Imines
by Vasco Corti, Enrico Marcantonio, Martina Mamone, Alessandro Giungi, Mariafrancesca Fochi and Luca Bernardi
Catalysts 2020, 10(2), 150; https://doi.org/10.3390/catal10020150 - 24 Jan 2020
Cited by 10 | Viewed by 3761
Abstract
The palladium-catalyzed (3 + 2) cycloaddition reaction between vinylcyclopropanes (VCPs) bearing geminal EWG’s and imines represents a straightforward and flexible entry to polysubstituted pyrrolidine derivatives. In this paper, we demonstrate that using a synergistic catalysis approach, based on the combination of phosphoric acid [...] Read more.
The palladium-catalyzed (3 + 2) cycloaddition reaction between vinylcyclopropanes (VCPs) bearing geminal EWG’s and imines represents a straightforward and flexible entry to polysubstituted pyrrolidine derivatives. In this paper, we demonstrate that using a synergistic catalysis approach, based on the combination of phosphoric acid and palladium catalysts, it is possible to engage for the first time N-aryl and N-benzyl imines in this cycloaddition reaction. A range of polysubstituted pyrrolidines is obtained with moderate to good yields and diastereoselectivities, using a simple palladium species (Pd(PPh3)4) and an archetypical phosphoric acid as catalyst combination. A two-step scheme which exploits the same palladium catalyst for two consecutive and mechanistically distinct reactions (the cycloaddition and a Suzuki–Miyaura cross-coupling) is also presented. This synergistic catalysis approach is well posited for the development of the enantioselective version of this reaction. A screening of common BINOL-derived chiral phosphoric acids as catalyst component identified a species giving the product with moderate, yet promising, enantioselectivity (64% ee). Full article
(This article belongs to the Special Issue Exploring Hydrogen Bond and Bronsted Acid Catalysis)
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