Evidence map›Paper›PMID 28424520›Full record

ArticleNature2017

Decarboxylative alkenylation.

Jacob T Edwards, Rohan R Merchant, Kyle S McClymont, Kyle W Knouse, Tian Qin, Lara R Malins, Benjamin Vokits, Scott A Shaw, Deng-Hui Bao, Fu-Liang Wei and 3 more

Abstract read
In one paragraph

Article in Nature, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 88 papers.

0numbers the graph read from it
0cells of the map it votes in
88citing 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

88 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Synthesis of Highly Substituted Alkenes from Terminal Alkynes.Journal of the American Chemical Society · 2025
    Article
  5. Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024
    Article
  14. Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024
    Article
  15. Article
  16. PrimaryFaraday discussions · 2023
    Article
  17. Article
  18. Article
  19. Article
  20. Article

28 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

13 authors.

Jacob T EdwardsDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Rohan R MerchantDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Kyle S McClymontDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Kyle W KnouseDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Tian QinDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Lara R MalinsDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Benjamin VokitsDiscovery Chemistry, Bristol-Myers Squibb, 350 Carter Road, Hopewell, New Jersey 08540, USA.
Scott A ShawDiscovery Chemistry, Bristol-Myers Squibb, 350 Carter Road, Hopewell, New Jersey 08540, USA.
Deng-Hui BaoAsymchem Life Science (Tianjin), Tianjin Economic-technological Development Zone, Tianjin 300457, China.
Fu-Liang WeiAsymchem Life Science (Tianjin), Tianjin Economic-technological Development Zone, Tianjin 300457, China.
Ting ZhouAsymchem Life Science (Tianjin), Tianjin Economic-technological Development Zone, Tianjin 300457, China.
Martin D EastgateChemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, USA.
Phil S BaranDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
A C-H Functionalization Approach to Heterocyclic Amino Acids for Application in Drug DiscoveryF32GM117816 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI MALINS, LARA REBECCA · 2016 to 2017
$96k
NIGMS NIH HHS F32 GM117816NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

Olefin chemistry, through pericyclic reactions, polymerizations, oxidations, or reductions, has an essential role in the manipulation of organic matter. Despite its importance, olefin synthesis still relies largely on chemistry introduced more than three decades ago, with metathesis being the most recent addition. Here we describe a simple method of accessing olefins with any substitution pattern or geometry from one of the most ubiquitous and variegated building blocks of chemistry: alkyl carboxylic acids. The activating principles used in amide-bond synthesis can therefore be used, with nickel- or iron-based catalysis, to extract carbon dioxide from a carboxylic acid and economically replace it with an organozinc-derived olefin on a molar scale. We prepare more than 60 olefins across a range of substrate classes, and the ability to simplify retrosynthetic analysis is exemplified with the preparation of 16 different natural products across 10 different families.

Indexed as

AlkenesAmidesBiological ProductsCarbon DioxideCarboxylic AcidsCatalysisIronNickelOxidation-ReductionPolyketidesSubstrate SpecificityTartratesZincAlkenesAmidesBiological ProductsCarbon DioxideCarboxylic Acidsdiethyl tartrateIronNickelPolyketidesTartratesZinc

Identifiers

PMID28424520
PMCPMC5478194

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.