Evidence map›Paper›PMID 28114300›Full record

ArticleNature2017

Molybdenum chloride catalysts for Z-selective olefin metathesis reactions.

Ming Joo Koh, Thach T Nguyen, Jonathan K Lam, Sebastian Torker, Jakub Hyvl, Richard R Schrock, Amir H Hoveyda

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 28 papers.

0numbers the graph read from it
0cells of the map it votes in
28citing 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

28 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
  4. 1,2-Difluoroethylene (HFO-1132): synthesis and chemistry.Beilstein journal of organic chemistry · 2024
    Review
  5. (Beilstein journal of organic chemistry · 2024
    Article
  6. Article
  7. Journal of the American Chemical Society · 2023
    Article
  8. Catalytic Cross-Metathesis Reactions That AffordJournal of the American Chemical Society · 2023
    Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Review
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Traceless Protection for More Broadly Applicable Olefin Metathesis.Angewandte Chemie (International ed. in English) · 2019
    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

7 authors.

Ming Joo KohDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Thach T NguyenDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Jonathan K LamDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Sebastian TorkerDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Jakub HyvlDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Richard R SchrockDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Amir H HoveydaDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.

Funding

Catalytic Stereoselective Olefin Metathesis ReactionsR01GM059426 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI HOVEYDA, AMIR H, SCHROCK, RICHARD R · 2000 to 2019
$10.0M
NIGMS NIH HHS R01 GM059426
6 · The paper itself

Abstract

The development of catalyst-controlled stereoselective olefin metathesis processes has been a pivotal recent advance in chemistry. The incorporation of appropriate ligands within complexes based on molybdenum, tungsten and ruthenium has led to reactivity and selectivity levels that were previously inaccessible. Here we show that molybdenum monoaryloxide chloride complexes furnish higher-energy (Z) isomers of trifluoromethyl-substituted alkenes through cross-metathesis reactions with the commercially available, inexpensive and typically inert Z-1,1,1,4,4,4-hexafluoro-2-butene. Furthermore, otherwise inefficient and non-stereoselective transformations with Z-1,2-dichloroethene and 1,2-dibromoethene can be effected with substantially improved efficiency and Z selectivity. The use of such molybdenum monoaryloxide chloride complexes enables the synthesis of representative biologically active molecules and trifluoromethyl analogues of medicinally relevant compounds. The origins of the activity and selectivity levels observed, which contradict previously proposed principles, are elucidated with the aid of density functional theory calculations.

Indexed as

AlkenesCatalysisChloridesFluorocarbonsLigandsMolybdenumAlkenesChloridesFluorocarbonsLigandsMolybdenummolybdenum chloride

Identifiers

PMID28114300
PMCPMC5748242

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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.