Literature DB >> 14527157

Cu(II)-nitroxyl radicals as catalytic galactose oxidase mimics.

Arné Dijksman1, Isabel W C E Arends, Roger A Sheldon.   

Abstract

Results from Hammett correlation studies and primary kinetic isotope effects for the CuCl-TEMPO catalysed aerobic benzyl alcohol oxidations are inconsistent with an oxoammonium based mechanism. We postulate a copper-mediated dehydrogenation mechanism, in which TEMPO regenerates the active Cu(II)-species. This mechanism is analogous to that observed for Galactose Oxidase and mimics thereof.

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Year:  2003        PMID： 14527157     DOI： 10.1039/b305941c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  14 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators.

Authors:  Artavazd Badalyan; Shannon S Stahl
Journal:  Nature       Date:  2016-06-27       Impact factor: 49.962

3.  Electronic Structure of a Cu(II)-Alkoxide Complex Modeling Intermediates in Copper-Catalyzed Alcohol Oxidations.

Authors:  Ellen C Hayes; Thomas R Porter; Charles J Barrows; Werner Kaminsky; James M Mayer; Stefan Stoll
Journal:  J Am Chem Soc       Date:  2016-03-18       Impact factor: 15.419

4.  Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols.

Authors:  Jessica M Hoover; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2011-10-03       Impact factor: 15.419

Review 5.  Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems.

Authors:  Bradford L Ryland; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

6.  Concerning the mechanism of the FeCl3-catalyzed alpha-oxyamination of aldehydes: evidence for a non-SOMO activation pathway.

Authors:  Jeffrey F Van Humbeck; Scott P Simonovich; Robert R Knowles; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

7.  Mechanism of alcohol oxidation mediated by copper(II) and nitroxyl radicals.

Authors:  Bradford L Ryland; Scott D McCann; Thomas C Brunold; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2014-08-14       Impact factor: 15.419

8.  Mechanism of copper(I)/TEMPO-catalyzed aerobic alcohol oxidation.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-01-31       Impact factor: 15.419

9.  Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential antidiabetic agents.

Authors:  Chitrala Teja; Spoorthy N Babu; Ayesha Noor; J Arul Daniel; S Asha Devi; Fazlur Rahman Nawaz Khan
Journal:  RSC Adv       Date:  2020-03-25       Impact factor: 4.036

10.  Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity.

Authors:  Jordan E Nutting; Kaining Mao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2021-07-07       Impact factor: 16.383
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