Literature DB >> 24039083

On the acidity and reactivity of highly effective chiral Brønsted acid catalysts: establishment of an acidity scale.

Karl Kaupmees1, Nikita Tolstoluzhsky, Sadiya Raja, Magnus Rueping, Ivo Leito.   

Abstract

Stronger acid, higher speed: The pKa  values of a range of binol-derived Brønsted acids of three different types were measured and found to correlate directly with the catalytic properties of the acids: higher rate constants kI were observed for more acidic Brønsted acid catalysts (see plot; binol=1,1'-bi-2-naphthol).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-triflylphosphoramides; Nazarov cyclization; acidity; organocatalysis; phosphoric acids

Year:  2013        PMID: 24039083     DOI: 10.1002/anie.201303605

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  13 in total

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3.  Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.

Authors:  Dennis A Kutateladze; Corin C Wagen; Eric N Jacobsen
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4.  Quantification of electrophilic activation by hydrogen-bonding organocatalysts.

Authors:  Ryan R Walvoord; Phuong N H Huynh; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2014-11-04       Impact factor: 15.419

5.  Palladium(0)-catalyzed asymmetric C(sp3)-H arylation using a chiral binol-derived phosphate and an achiral ligand.

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Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

6.  Disulfonimides versus Phosphoric Acids in Brønsted Acid Catalysis: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Reactivity.

Authors:  Kerstin Rothermel; Matej Žabka; Johnny Hioe; Ruth M Gschwind
Journal:  J Org Chem       Date:  2019-10-02       Impact factor: 4.354

7.  Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.

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Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825

8.  Association Equilibria of Organo-Phosphoric Acids with Imines from a Combined Dielectric and Nuclear Magnetic Resonance Spectroscopy Approach.

Authors:  Christian Dreier; Leon Prädel; Amelie A Ehrhard; Manfred Wagner; Johannes Hunger
Journal:  Anal Chem       Date:  2021-02-18       Impact factor: 6.986

9.  Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles.

Authors:  Pinglu Zhang; Nobuya Tsuji; Jie Ouyang; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-01-05       Impact factor: 15.419

10.  Diazaphosphinanes as hydride, hydrogen atom, proton or electron donors under transition-metal-free conditions: thermodynamics, kinetics, and synthetic applications.

Authors:  Jingjing Zhang; Jin-Dong Yang; Jin-Pei Cheng
Journal:  Chem Sci       Date:  2020-03-05       Impact factor: 9.825

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