Literature DB >> 34609137

"How Should I Think about Voltage? What Is Overpotential?": Establishing an Organic Chemistry Intuition for Electrochemistry.

Jordan E Nutting1, James B Gerken1, Alexios G Stamoulis1, David L Bruns1, Shannon S Stahl1.   

Abstract

Redox reactions are ubiquitous in organic synthesis and intrinsic to organic electrosynthesis. The language and concepts used to describe reactions in these domains are sufficiently different to create barriers that hinder broader adoption and understanding of electrochemical methods. To bridge these gaps, this Synopsis compares chemical and electrochemical redox reactions, including concepts of free energy, voltage, kinetic barriers, and overpotential. This discussion is intended to increase the accessibility of electrochemistry for organic chemists lacking formal training in this area.

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Year:  2021        PMID: 34609137      PMCID: PMC8604791          DOI: 10.1021/acs.joc.1c01520

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  28 in total

1.  Visible light photoredox catalysis: applications in organic synthesis.

Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

Review 2.  Thermochemistry of proton-coupled electron transfer reagents and its implications.

Authors:  Jeffrey J Warren; Tristan A Tronic; James M Mayer
Journal:  Chem Rev       Date:  2010-10-06       Impact factor: 60.622

3.  Electrochemical Strategy for Hydrazine Synthesis: Development and Overpotential Analysis of Methods for Oxidative N-N Coupling of an Ammonia Surrogate.

Authors:  Fei Wang; James B Gerken; Desiree M Bates; Yeon Jung Kim; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2020-06-29       Impact factor: 15.419

Review 4.  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

5.  Accurate oxidation potentials of benzene and biphenyl derivatives via electron-transfer equilibria and transient kinetics.

Authors:  Paul B Merkel; Pu Luo; Joseph P Dinnocenzo; Samir Farid
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

6.  Concepts and tools for mechanism and selectivity analysis in synthetic organic electrochemistry.

Authors:  Cyrille Costentin; Jean-Michel Savéant
Journal:  Proc Natl Acad Sci U S A       Date:  2019-05-17       Impact factor: 11.205

7.  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

8.  Standard Reduction Potentials for Oxygen and Carbon Dioxide Couples in Acetonitrile and N,N-Dimethylformamide.

Authors:  Michael L Pegis; John A S Roberts; Derek J Wasylenko; Elizabeth A Mader; Aaron M Appel; James M Mayer
Journal:  Inorg Chem       Date:  2015-12-07       Impact factor: 5.165

Review 9.  Electrifying Organic Synthesis.

Authors:  Anton Wiebe; Tile Gieshoff; Sabine Möhle; Eduardo Rodrigo; Michael Zirbes; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

Review 10.  Electrode Materials in Modern Organic Electrochemistry.

Authors:  David M Heard; Alastair J J Lennox
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-24       Impact factor: 15.336

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  5 in total

1.  Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis.

Authors:  Md Asmaul Hoque; Jack Twilton; Jieru Zhu; Matthew D Graaf; Kaid C Harper; Emilian Tuca; Gino A DiLabio; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2022-08-16       Impact factor: 16.383

Review 2.  Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors:  David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal:  J Org Chem       Date:  2022-06-07       Impact factor: 4.198

3.  Modular terpene synthesis enabled by mild electrochemical couplings.

Authors:  Stephen J Harwood; Maximilian D Palkowitz; Cara N Gannett; Paulo Perez; Zhen Yao; Lijie Sun; Héctor D Abruña; Scott L Anderson; Phil S Baran
Journal:  Science       Date:  2022-02-17       Impact factor: 63.714

4.  Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.

Authors:  Chad E Hatch; Maxwell I Martin; Philip H Gilmartin; Lu Xiong; Danielle J Beam; Glenn P A Yap; Matthew J Von Bargen; Joel Rosenthal; William J Chain
Journal:  Org Lett       Date:  2022-02-11       Impact factor: 6.072

5.  Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates.

Authors:  Kouichi Matsumoto; Yuta Hayashi; Kengo Hamasaki; Mizuki Matsuse; Hiyono Suzuki; Keiji Nishiwaki; Norihito Kawashita
Journal:  Beilstein J Org Chem       Date:  2022-08-29       Impact factor: 2.544

  5 in total

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