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Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry

Luca, Oana R. and Gustafson, Jeffrey L. and Maddox, Sean M. and Fenwick, Aidan Q. and Smith, Daryl C. (2015) Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry. Organic Chemistry Frontiers, 2 (7). pp. 823-848. ISSN 2052-4110. https://resolver.caltech.edu/CaltechAUTHORS:20150518-084926507

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Abstract

The present review surveys current chemical understanding of catalysis by addition and removal of an electron. As an overarching theme of this type of catalysis, we introduce the role of redox scales in oxidation and reduction reactions as a direct analogue of pK_a scales in acid/base catalysis. Each scale is helpful in determining the type of reactivity to be expected. In addition, we describe several means of generating electrons and holes via chemical reactions, plasmonic resonance, radiolytic, photochemical and electrochemical methods. We specifically draw parallels between the now well-established fields of photoredox catalysis and chemical opportunities made available by electrochemical methods. We highlight accessible potential ranges for a series of electrochemical solvents and provide a discussion on experimental design, pitfalls and some remaining challenges in preparative organic electrochemistry.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c5qo00075kDOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2015/QO/C5QO00075KPublisherArticle
ORCID:
AuthorORCID
Luca, Oana R.0000-0002-2988-4909
Fenwick, Aidan Q.0000-0003-4442-0878
Additional Information:© 2015 the Partner Organisations. Received 5th March 2015, Accepted 15th April 2015. First published online 07 May 2015. This material is based upon work performed by the Joint Center for Artificial Photosynthesis, a DOE Energy Innovation Hub, supported through the Office of Science of the U.S. Department of Energy under Award Number DE-SC0004993. JLG would like to thank SDSU for startup funds. We thank Dr Charles McCrory, Dr John Gregoire, Dr James Blakemore, Dr Kevin Oberg, Mr Chris Nalbandian, Dr Corinne Allen and Professors Donna Blackmond, Carl Koval, Keary Engle, Phil Baran, Robert Crabtree, Seth Herzon, Jonas Peters, T. Don Tilley, Clifford Kubiak and Nathan Lewis for insightful discussions.
Funders:
Funding AgencyGrant Number
Department of Energy (DOE)DE-SC0004993
San Diego State UniversityUNSPECIFIED
Issue or Number:7
Record Number:CaltechAUTHORS:20150518-084926507
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150518-084926507
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57582
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:18 May 2015 20:00
Last Modified:03 Oct 2019 08:26

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