Literature DB >> 21473575

Highly efficient, organocatalytic aerobic alcohol oxidation.

Masatoshi Shibuya1, Yuji Osada, Yusuke Sasano, Masaki Tomizawa, Yoshiharu Iwabuchi.   

Abstract

5-Fluoro-2-azaadamantane N-oxyl (5-F-AZADO) realizes a simple, organocatalytic aerobic alcohol oxidation system that has a wide scope under mild conditions at ambient pressure and temperature and is weakly acidic and halogen- and transition-metal-free. The oxoammonium nitrate (5-F-AZADO(+)NO(3)(-)) works as a bifunctional catalyst of 5-F-AZADO and NO(x) that enables the catalytic aerobic oxidation of alcohols by itself (a metal-salt-free system).
© 2011 American Chemical Society

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Year:  2011        PMID： 21473575     DOI： 10.1021/ja110940c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

1.  Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.

Authors:  Juno C Siu; Joseph B Parry; Song Lin
Journal:  J Am Chem Soc       Date:  2019-01-28       Impact factor: 15.419

2.  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

3.  Mediated Fuel Cells: Soluble Redox Mediators and Their Applications to Electrochemical Reduction of O2 and Oxidation of H2, Alcohols, Biomass, and Complex Fuels.

Authors:  Colin W Anson; Shannon S Stahl
Journal:  Chem Rev       Date:  2020-03-27       Impact factor: 60.622

4.  Nitrate as a Redox Co-Catalyst for the Aerobic Pd-Catalyzed Oxidation of Unactivated sp(3)-C-H Bonds.

Authors:  Kara J Stowers; Asako Kubota; Melanie S Sanford
Journal:  Chem Sci       Date:  2012-08-30       Impact factor: 9.825

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

6.  Highly efficient Cu(I)-catalyzed oxidation of alcohols to ketones and aldehydes with diaziridinone.

Authors:  Yingguang Zhu; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2013-02-15       Impact factor: 6.005

Review 7.  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

8.  Electrocatalytic Alcohol Oxidation with TEMPO and Bicyclic Nitroxyl Derivatives: Driving Force Trumps Steric Effects.

Authors:  Mohammad Rafiee; Kelsey C Miles; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2015-11-13       Impact factor: 15.419

9.  High-Potential Electrocatalytic O2 Reduction with Nitroxyl/NO x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis.

Authors:  James B Gerken; Shannon S Stahl
Journal:  ACS Cent Sci       Date:  2015-07-15       Impact factor: 14.553

10.  CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides.

Authors:  Kengo Kataoka; Keiju Wachi; Xiongjie Jin; Kosuke Suzuki; Yusuke Sasano; Yoshiharu Iwabuchi; Jun-Ya Hasegawa; Noritaka Mizuno; Kazuya Yamaguchi
Journal:  Chem Sci       Date:  2018-05-07       Impact factor: 9.825
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