Literature DB >> 28358089

Exploiting non-covalent π interactions for catalyst design.

Andrew J Neel1,2, Margaret J Hilton3, Matthew S Sigman3, F Dean Toste1,2.   

Abstract

Molecular recognition, bi<span class="Chemical">nding and cata<class="Chemical">span class="Chemical">lysis are often mediated by non-covalent interactions involving aromatic functional groups. Although the relative complexity of these so-called π interactions has made them challenging to study, theory and modelling have now reached the stage at which we can explain their physical origins and obtain reliable insight into their effects on molecular binding and chemical transformations. This offers opportunities for the rational manipulation of these complex non-covalent interactions and their direct incorporation into the design of small-molecule catalysts and enzymes.

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Year:  2017        PMID: 28358089      PMCID: PMC5907483          DOI: 10.1038/nature21701

Source DB:  PubMed          Journal:  Nature        ISSN: 0028-0836            Impact factor:   49.962


  85 in total

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Authors:  Jennifer C. Ma; Dennis A. Dougherty
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

2.  Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts.

Authors:  Robert R Knowles; Eric N Jacobsen
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-18       Impact factor: 11.205

3.  Relevant anion-π interactions in biological systems: the case of urate oxidase.

Authors:  Carolina Estarellas; Antonio Frontera; David Quiñonero; Pere M Deyà
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-10       Impact factor: 15.336

4.  High-accuracy quantum mechanical studies of pi-pi interactions in benzene dimers.

Authors:  Mutasem Omar Sinnokrot; C David Sherrill
Journal:  J Phys Chem A       Date:  2006-09-21       Impact factor: 2.781

5.  Anion-π Catalysis of Enolate Chemistry: Rigidified Leonard Turns as a General Motif to Run Reactions on Aromatic Surfaces.

Authors:  Yoann Cotelle; Sebastian Benz; Alyssa-Jennifer Avestro; Thomas R Ward; Naomi Sakai; Stefan Matile
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-24       Impact factor: 15.336

6.  Demonstration of the existence of intermolecular lone pair...pi interaction between alcoholic oxygen and the C(6)F(5) group in organic solvent.

Authors:  Toshinobu Korenaga; Taeko Shoji; Kazutaka Onoue; Takashi Sakai
Journal:  Chem Commun (Camb)       Date:  2009-06-23       Impact factor: 6.222

7.  Aromatic interactions as control elements in stereoselective organic reactions.

Authors:  Elizabeth H Krenske; K N Houk
Journal:  Acc Chem Res       Date:  2012-07-24       Impact factor: 22.384

8.  Anion-π interactions and positive electrostatic potentials of N-heterocycles arise from the positions of the nuclei, not changes in the π-electron distribution.

Authors:  Steven E Wheeler; Jacob W G Bloom
Journal:  Chem Commun (Camb)       Date:  2014-10-04       Impact factor: 6.222

9.  Carbohydrate-aromatic interactions.

Authors:  Juan Luis Asensio; Ana Ardá; Francisco Javier Cañada; Jesús Jiménez-Barbero
Journal:  Acc Chem Res       Date:  2012-06-15       Impact factor: 22.384

10.  Noncovalent Lone Pair⋅⋅⋅(No-π!)-Heteroarene Interactions: The Janus-Faced Hydroxy Group.

Authors:  Ilias Pavlakos; Tanzeel Arif; Abil E Aliev; William B Motherwell; Graham J Tizzard; Simon J Coles
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-27       Impact factor: 15.336

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2.  Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst.

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3.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

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5.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

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6.  Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors:  Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
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7.  Structure-Activity Studies of Semiochemicals from the Spider Orchid Caladenia plicata for Sexual Deception.

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8.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

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9.  Cyclic di-AMP, a second messenger of primary importance: tertiary structures and binding mechanisms.

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10.  Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

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Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

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