Evidence map›Paper›PMID 38574151›Full record

ArticleScience (New York, N.Y.)2024

Carbon quaternization of redox active esters and olefins by decarboxylative coupling.

Xu-Cheng Gan, Benxiang Zhang, Nathan Dao, Cheng Bi, Maithili Pokle, Liyan Kan, Michael R Collins, Chet C Tyrol, Philippe N Bolduc, Michael Nicastri and 3 more

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 25 papers.

0numbers the graph read from it
0cells of the map it votes in
25citing 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

25 citing papers in PubMed.

  1. Article
  2. Nickel-Catalyzed Radical-Radical Cross-Coupling Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  3. Article
  4. Oxyalkylation of Alkenes via Triple Radical Sorting.Journal of the American Chemical Society · 2026
    Article
  5. Article
  6. Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026
    Article
  7. Boron-Mediated Hydroalkylation of Unactivated Olefins: AnJournal of the American Chemical Society · 2026
    Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Bimolecular Homolytic Substitution (SACS central science · 2025
    Review
  16. Article
  17. Radical Sorting Catalysis via Bimolecular Homolytic Substitution (SJournal of the American Chemical Society · 2025
    Review
  18. Article
  19. Aminoalkylation of Alkenes Enabled by Triple Radical Sorting.Journal of the American Chemical Society · 2025
    Article
  20. Low-energy photoredox catalysis.Nature reviews. Chemistry · 2025
    Review
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

13 authors.

Xu-Cheng Gan *Department of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0001-7404-3087
Benxiang Zhang *Department of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0009-0009-6787-2288
Nathan Dao *Department of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0003-4116-491X
Cheng BiDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0002-9332-9918
Maithili PokleDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.
Liyan KanDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0009-0009-3986-5910
Michael R CollinsOncology Medicinal Chemistry Department, Pfizer Pharmaceuticals, San Diego, CA 92122, USA.ORCID 0000-0001-7799-1664
Chet C TyrolPfizer Medicine Design, Groton, CT 06340, USA.ORCID 0009-0000-0121-8544
Philippe N BolducBiogen Inc., Cambridge, MA 02142, USA.ORCID 0000-0001-8726-4364
Michael NicastriBiogen Inc., Cambridge, MA 02142, USA.ORCID 0000-0002-6283-5543
Yu KawamataDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0002-5515-9612
Phil S BaranDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0001-9193-9053
Ryan ShenviDepartment of Chemistry, Scripps Research, La Jolla, CA 92037, USA.ORCID 0000-0001-8353-6449

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
Unusual Pharmacophores and New Tools for Cross-CouplingR35GM122606 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI Ryan Ashok Shenvi · 2017 to 2026
$7.1M
NIGMS NIH HHS R35 GM118176NIGMS NIH HHS R35 GM122606
6 · The paper itself

Abstract

The synthesis of quaternary carbons often requires numerous steps and complex conditions or harsh reagents that act on heavily engineered substrates. This is largely a consequence of conventional polar-bond retrosynthetic disconnections that in turn require multiple functional group interconversions, redox manipulations, and protecting group chemistry. Here, we report a simple catalyst and reductant combination that converts two types of feedstock chemicals, carboxylic acids and olefins, into tetrasubstituted carbons through quaternization of radical intermediates. An iron porphyrin catalyst activates each substrate by electron transfer or hydrogen atom transfer, and then combines the fragments using a bimolecular homolytic substitution (S

Identifiers

PMID38574151
PMCPMC11452921

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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.