Literature DB >> 19746477

Catalytic activity dependency on catalyst components in aerobic copper-TEMPO oxidation.

Esa T T Kumpulainen1, Ari M P Koskinen.   

Abstract

The influence of catalyst components in the copper-TEMPO (2,2,6,6-tetramethylpiperidine N-oxide) catalysed aerobic oxidation of alcohols was investigated. The type and amount of base greatly influences reactivity. The bipyridyl ligand concentration had no major influence on catalysis, but excessive amounts led to a decrease in activity for longer reaction times. The kinetic dependency for TEMPO was found to be 1.15, and for copper 2.25, which is an indication of a binuclear catalytic system. Optimised conditions with various allylic and aliphatic alcohols give good to excellent rapid oxidations.

Entities:  

Year:  2009        PMID: 19746477     DOI: 10.1002/chem.200901245

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  21 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.  Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature.

Authors:  Jinho Kim; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-07-05       Impact factor: 13.084

3.  KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.

Authors:  Kelsey C Miles; M Leigh Abrams; Clark R Landis; Shannon S Stahl
Journal:  Org Lett       Date:  2016-07-13       Impact factor: 6.005

4.  Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis.

Authors:  Paige E Piszel; Aristidis Vasilopoulos; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-24       Impact factor: 15.336

5.  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 6.  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

7.  Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines.

Authors:  Susan L Zultanski; Jingyi Zhao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2016-05-16       Impact factor: 15.419

8.  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

9.  Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-11-01       Impact factor: 13.084

10.  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

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