Abstract
Proton-coupled electron transfers (PCETs) are unconventional redox processes in which both protons and electrons are exchanged, often in a concerted elementary step. While PCET is now recognized to play a central a role in biological redox catalysis and inorganic energy conversion technologies, its applications in organic synthesis are only beginning to be explored. In this chapter, we aim to highlight the origins, development, and evolution of the PCETprocessesmost relevant to applications in organic synthesis.Particularemphasis is given to the ability ofPCETto serve as a nonclassical mechanism for homolytic bond activation that is complimentary to more traditional hydrogen atom transfer processes, enabling the direct generation of valuable organic radical intermediates directly from their native functional group precursors under comparatively mild catalytic conditions. The synthetically advantageous features of PCET reactivity are described in detail, along with examples from the literature describing the PCET activation of common organic functional groups.
Keywords
This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J.Ramón.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Miller, D.C., Tarantino, K.T., Knowles, R.R. (2016). Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities. In: Guillena, G., Ramón, D. (eds) Hydrogen Transfer Reactions. Topics in Current Chemistry Collections. Springer, Cham. https://doi.org/10.1007/978-3-319-43051-5_4
Download citation
DOI: https://doi.org/10.1007/978-3-319-43051-5_4
Received:
Accepted:
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-43049-2
Online ISBN: 978-3-319-43051-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)