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Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

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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 PCET processes most relevant to applications in organic synthesis. Particular emphasis is given to the ability of PCET to serve as a non-classical 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.

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Adapted with permission from [136]. Copyright 1998 American Chemical Society

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Reproduced with permission from [1]. Copyright 2014 American Chemical Society. This article may be accessed online at the following URL: http://pubs.acs.org/doi/pdf/10.1021/cr4006654

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Figures reprinted with permission from [222]. Copyright 2015 American Chemical Society. This article may be accessed online at the following URL: http://pubs.acs.org/doi/pdf/10.1021/jacs.5b09671

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Adapted with permission from [233]. Copyright 2015 American Chemical Society

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Reproduced from [242] with permission of the Royal Society of Chemistry

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Acknowledgments

We gratefully acknowledge the NIH (R01 GM113105) for financial support.

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  1. Department of Chemistry, Princeton University, Princeton, NJ, 08544, USA

    David C. Miller, Kyle T. Tarantino & Robert R. Knowles

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  1. David C. Miller
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  2. Kyle T. Tarantino
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Correspondence to Robert R. Knowles.

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This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J. Ramón.

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Miller, D.C., Tarantino, K.T. & Knowles, R.R. Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities. Top Curr Chem (Z) 374, 30 (2016). https://doi.org/10.1007/s41061-016-0030-6

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