Evidence map›Paper›PMID 31650673›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Site-Selective Alkoxylation of Benzylic C-H Bonds by Photoredox Catalysis.

Byung Joo Lee, Kimberly S DeGlopper, Tehshik P Yoon

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.

0numbers the graph read from it
0cells of the map it votes in
38citing 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

38 citing papers in PubMed.

  1. Article
  2. Article
  3. Copper-Catalyzed Three-Component Selective 1,4-Amino Oxygenation of 1,3-Dienes.Angewandte Chemie (International ed. in English) · 2026
    Article
  4. Review
  5. Article
  6. Article
  7. Sustainable Approaches for the Protection and Deprotection of Functional Groups.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Review
  8. A General Strategy for C(spAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  9. Article
  10. C(spACS catalysis · 2025
    Article
  11. Article
  12. Direct Benzylic C-H Etherification Enabled by Base-Promoted Halogen Transfer.Angewandte Chemie (International ed. in English) · 2024
    Article
  13. Article
  14. Total Synthesis of Dragocins A-C through Electrochemical Cyclization.Angewandte Chemie (International ed. in English) · 2024
    Article
  15. Article
  16. Review
  17. Polar Heterobenzylic C(spJournal of the American Chemical Society · 2023
    Article
  18. Article
  19. Review
  20. Article
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

3 authors.

Byung Joo LeeDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, USA.ORCID 0000-0002-0078-7865
Kimberly S DeGlopperDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, USA.
Tehshik P YoonDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, USA.ORCID 0000-0002-3934-4973

Funding

Visible Light PhotocatalysisR01GM095666 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI YOON, TEHSHIK P · 2011 to 2022
$4.2M
NIGMS NIH HHS GM095666NIGMS NIH HHS R01 GM095666
6 · The paper itself

Abstract

Methods that enable the direct C-H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C-N and C-C bond formation. In particular, almost all methods for the incorporation of alcohols by C-H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C-H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C-O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.

Indexed as

AlcoholsCarbonCatalysisHumansHydrogenOxidation-ReductionAlcoholsalkoxyl radicalCarbonHydrogenalcoholscopperoxidationphotocatalysisradicals

Identifiers

PMID31650673
PMCPMC6923605

What OpenQuestion holds

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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.