Evidence map›Paper›PMID 39325876›Full record

ArticleScience (New York, N.Y.)2024

Photochemical phosphorus-enabled scaffold remodeling of carboxylic acids.

Qiupeng Peng, Meemie U Hwang, Ángel Rentería-Gómez, Poulami Mukherjee, Ryan M Young, Yunfan Qiu, Michael R Wasielewski, Osvaldo Gutierrez, Karl A Scheidt

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Radical Sampling Enabled Saturated N-Heterocycle Cyclization.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
  5. Photoenolization ofJournal of the American Chemical Society · 2025
    Article
  6. 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

9 authors.

Qiupeng PengDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0000-0002-5501-3947
Meemie U HwangDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0009-0008-4520-8389
Ángel Rentería-GómezDepartment of Chemistry, Texas A&M University, College Station, TX 77843, USA.ORCID 0000-0002-9411-8805
Poulami MukherjeeDepartment of Chemistry, Texas A&M University, College Station, TX 77843, USA.ORCID 0000-0002-2876-7612
Ryan M YoungDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0000-0002-5108-0261
Yunfan QiuDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0000-0002-4666-1424
Michael R WasielewskiDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0000-0003-2920-5440
Osvaldo GutierrezDepartment of Chemistry, Texas A&M University, College Station, TX 77843, USA.ORCID 0000-0001-8151-7519
Karl A ScheidtDepartment of Chemistry, Northwestern University, Evanston, IL 60208, USA.ORCID 0000-0003-4856-3569

Funding

New Cooperative Catalysis Concepts for Asymmetric SynthesisR35GM136440 · NIGMS · NORTHWESTERN UNIVERSITY · PI Karl A Scheidt · 2020 to 2026
$2.9M
New Directions in Sustainable Open-Shell Radical C-C Bond Formations Enabled by Merging Modern Computational and Experimental MethodsR35GM137797 · NIGMS · UNIV OF MARYLAND, COLLEGE PARK · PI Osvaldo Gutierrez · 2020 to 2026
$2.7M
NIGMS NIH HHS R35 GM136440NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

The excitation of carbonyl compounds by light to generate radical intermediates has historically been restricted to ketones and aldehydes; carboxylic acids have been overlooked because of high energy requirements and low quantum efficiency. A successful activation strategy would necessitate a bathochromic shift in the absorbance profile, an increase in triplet diradical lifetime, and ease of further functionalization. We present a single-flask transformation of carboxylic acids to acyl phosphonates that can access synthetically useful triplet diradicals under visible light or near-ultraviolet irradiation. The use of phosphorus circumvents unproductive Norrish type I processes, promoting selectivity that enables hydrogen-atom transfer reactivity. Use of this strategy promotes the efficient scaffold remodeling of carboxylic acids through various annulation, contraction, and expansion manifolds.

Identifiers

PMID39325876
PMCPMC11780707

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Registered trials

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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.