Literature DB >> 22337651

TEMPO-mediated electrooxidation of primary and secondary alcohols in a microfluidic electrolytic cell.

Joseph T Hill-Cousins1, Jekaterina Kuleshova, Robert A Green, Peter R Birkin, Derek Pletcher, Toby J Underwood, Stuart G Leach, Richard C D Brown.   

Abstract

A general procedure for the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated electrooxidation of primary and secondary alcohols modified for application in a microfluidic electrolytic cell is described. The electrocatalytic system utilises a buffered aqueous tert-butanol reaction medium, which operates effectively without the requirement for additional electrolyte, providing a mild protocol for the oxidation of alcohols to aldehydes and ketones at ambient temperature on a laboratory scale. Optimisation of the process is discussed along with the oxidation of 15 representative alcohols.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22337651     DOI： 10.1002/cssc.201100601

Source DB:  PubMed          Journal:  ChemSusChem        ISSN： 1864-5631            Impact factor:   8.928


  9 in total

Review 1.  Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.

Authors:  Jordan E Nutting; Mohammad Rafiee; Shannon S Stahl
Journal:  Chem Rev       Date:  2018-04-30       Impact factor: 60.622

2.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

3.  Scalable Flow Electrochemical Alcohol Oxidation: Maintaining High Stereochemical Fidelity in the Synthesis of Levetiracetam.

Authors:  Xing Zhong; Md Asmaul Hoque; Matthew D Graaf; Kaid C Harper; Fei Wang; J David Genders; Shannon S Stahl
Journal:  Org Process Res Dev       Date:  2021-04-19       Impact factor: 3.317

Review 4.  Advances in electro- and sono-microreactors for chemical synthesis.

Authors:  Tomas Hardwick; Nisar Ahmed
Journal:  RSC Adv       Date:  2018-06-19       Impact factor: 4.036

5.  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

Review 6.  Electrochemical Alcohol Oxidation Mediated by TEMPO-like Nitroxyl Radicals.

Authors:  Rosaria Ciriminna; Mina Ghahremani; Babak Karimi; Mario Pagliaro
Journal:  ChemistryOpen       Date:  2017-01-11       Impact factor: 2.911

Review 7.  Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products.

Authors:  Sabine Möhle; Michael Zirbes; Eduardo Rodrigo; Tile Gieshoff; Anton Wiebe; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-19       Impact factor: 15.336

8.  Direct electrochemical oxidation of alcohols with hydrogen evolution in continuous-flow reactor.

Authors:  Dan Wang; Pan Wang; Shengchun Wang; Yi-Hung Chen; Heng Zhang; Aiwen Lei
Journal:  Nat Commun       Date:  2019-06-26       Impact factor: 14.919

9.  Direct and Indirect Electrooxidation of Glycerol to Value-Added Products.

Authors:  Michael Guschakowski; Uwe Schröder
Journal:  ChemSusChem       Date:  2021-05-18       Impact factor: 9.140
  9 in total

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