Evidence map›Paper›PMID 34813277›Full record

ReviewChemical reviews2022

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Philip R D Murray, James H Cox, Nicholas D Chiappini, Casey B Roos, Elizabeth A McLoughlin, Benjamin G Hejna, Suong T Nguyen, Hunter H Ripberger, Jacob M Ganley, Elaine Tsui and 4 more

Abstract readReview
In one paragraph

Review in Chemical reviews, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 141 papers.

0numbers the graph read from it
0cells of the map it votes in
141citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

141 citing papers in PubMed.

  1. Net fluorine atom transfer from the perspective of a PCET chemist.Chemical communications (Cambridge, England) · 2026
    Review
  2. Mapping Proton-Coupled Electron Transfer With Real Space Coordinates.Angewandte Chemie (International ed. in English) · 2026
    Article
  3. Article
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  11. Unveiling the Potential ofJournal of the American Chemical Society · 2026
    Article
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  14. Article
  15. Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  16. Article
  17. Article
  18. Article
  19. Review
  20. Article

81 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

14 authors.

Philip R D MurrayDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0001-7873-5232
James H CoxDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-1631-3031
Nicholas D ChiappiniDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-0469-1008
Casey B RoosDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-2734-5848
Elizabeth A McLoughlinDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-1481-266X
Benjamin G HejnaDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Suong T NguyenDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-5745-9096
Hunter H RipbergerDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-3146-9579
Jacob M GanleyDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0001-7705-2886
Elaine TsuiDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-5872-4824
Nick Y ShinDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-3132-502X
Brian KoronkiewiczDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0002-9892-7837
Guanqi QiuDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-3818-3896
Robert R KnowlesDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-1044-4900

Funding

New Synthetic Methods Enabled by Excited-State Redox ChemistryR35GM134893 · NIGMS · PRINCETON UNIVERSITY · PI Robert R Knowles · 2020 to 2026
$3.8M
Organobismuth Compounds As Universal Precursors for Oxidative and Reductive Radical Group Transfer via Photoredox CatalysisF32GM142190 · NIGMS · PRINCETON UNIVERSITY · PI CHIAPPINI, NICHOLAS D · 2021 to 2022
$88k
NIGMS NIH HHS F32 GM142190NIGMS NIH HHS R35 GM134893
6 · The paper itself

Abstract

We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner's guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N-H, O-H, S-H, and C-H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X═Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

Indexed as

ElectronsProtonsChemistry Techniques, SyntheticElectron TransportOxidation-ReductionProtons

Identifiers

PMID34813277
PMCPMC8796287

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.