Evidence map›Paper›PMID 28094980›Full record

ArticleJournal of the American Chemical Society2017

Fe-Catalyzed C-C Bond Construction from Olefins via Radicals.

Julian C Lo, Dongyoung Kim, Chung-Mao Pan, Jacob T Edwards, Yuki Yabe, Jinghan Gui, Tian Qin, Sara Gutiérrez, Jessica Giacoboni, Myles W Smith and 2 more

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 96 papers.

0numbers the graph read from it
0cells of the map it votes in
96citing papers in PubMed
20.8field-weighted citation impact, top 1% of its field
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

96 citing papers in PubMed, 421 citations in OpenAlex.

  1. Article
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  6. Review
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  9. An Oxygen Walk Approach for C3 Selective Hydroxylation of Pyridines.Synlett : accounts and rapid communications in synthetic organic chemistry · 2025
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  11. Enantioselective Access to Decahydroquinolines Bearing a CThe Journal of organic chemistry · 2025
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  15. Review
  16. Building Catalytic Reactions One Electron at a Time.Accounts of chemical research · 2024
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  17. Total Synthesis of Hypersampsone M.Journal of the American Chemical Society · 2024
    Article
  18. Article
  19. Directed Hydrogen Atom Transfer for Selective Reactions of Polyenols.Journal of the American Chemical Society · 2024
    Article
  20. Article

36 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

12 authors at 2 institutions in 1 country.

Julian C LoDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Dongyoung KimDepartment of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520, United States.
Chung-Mao PanDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Jacob T EdwardsDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Yuki YabeDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Jinghan GuiDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID 0000-0002-4786-5779
Tian QinDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Sara GutiérrezDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Jessica GiacoboniDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Myles W SmithDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Patrick L HollandDepartment of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520, United States.ORCID 0000-0002-2883-2031
Phil S BaranDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID 0000-0001-9193-9053
Scripps Research Institute · USYale University · US

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor and acceptor olefins. Although the substitution on the donor olefins was initially limited to alkyl and aryl groups, additional efforts culminated in the expansion of the scope of the substitution to various heteroatom-based functionalities, providing a unified olefin reactivity. A vinyl sulfone acceptor olefin was developed, which allowed for the efficient synthesis of sulfone adducts that could be used as branch points for further diversification. Moreover, this reactivity was extended into an olefin-based Minisci reaction to functionalize heterocyclic scaffolds. Finally, mechanistic studies resulted in a more thorough understanding of the reaction, giving rise to the development of a more efficient second-generation set of olefin cross-coupling conditions.

Indexed as

AlkenesCatalysisFree RadicalsIron CompoundsMolecular StructureSulfonesAlkenesFree RadicalsIron CompoundsSulfones

Identifiers

PMID28094980
PMCPMC5314431
OpenAlexW2578365198

What OpenQuestion holds

Textmetadata
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.