Evidence map›Paper›PMID 31310528›Full record

ArticleJournal of the American Chemical Society2019

A Supramolecular Strategy for Selective Catalytic Hydrogenation Independent of Remote Chain Length.

Trandon A Bender, Robert G Bergman, Kenneth N Raymond, F Dean Toste

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.

0numbers the graph read from it
0cells of the map it votes in
21citing 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

21 citing papers in PubMed.

  1. Article
  2. Review
  3. Article
  4. Review
  5. Article
  6. Review
  7. Article
  8. Article
  9. Review
  10. Article
  11. Differentiable Formation of Chiroptical Lanthanide Heterometallic LnChemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  12. Site-selective reactions mediated by molecular containers.Beilstein journal of organic chemistry · 2022
    Review
  13. Review
  14. Heteroleptic Ligation by an endo-Functionalized Cage.Angewandte Chemie (International ed. in English) · 2021
    Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. 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

4 authors.

Trandon A BenderChemical Sciences Division, Lawrence Berkeley National Laboratory, and Department of Chemistry , University of California, Berkeley , Berkeley , California 94720-1460 , United States.
Robert G BergmanChemical Sciences Division, Lawrence Berkeley National Laboratory, and Department of Chemistry , University of California, Berkeley , Berkeley , California 94720-1460 , United States.
Kenneth N RaymondChemical Sciences Division, Lawrence Berkeley National Laboratory, and Department of Chemistry , University of California, Berkeley , Berkeley , California 94720-1460 , United States.ORCID 0000-0001-6968-9801
F Dean TosteChemical Sciences Division, Lawrence Berkeley National Laboratory, and Department of Chemistry , University of California, Berkeley , Berkeley , California 94720-1460 , United States.ORCID 0000-0001-8018-2198

Funding

Investigating the unification of supramolecular and organometallic catalysis for new reaction developmentF32GM129933 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI BENDER, TRANDON ALLEN · 2018 to 2020
$136k
NIGMS NIH HHS F32 GM129933
6 · The paper itself

Abstract

Performing selective transformations on complex substrates remains a challenge in synthetic chemistry. These difficulties often arise due to cross-reactivity, particularly in the presence of similar functional groups at multiple sites. Therefore, there is a premium on the ability to perform selective activation of these functional groups. We report here a supramolecular strategy where encapsulation of a hydrogenation catalyst enables selective olefin hydrogenation, even in the presence of multiple sites of unsaturation. While the reaction requires at least one sterically nondemanding alkene substituent, the rate of hydrogenation is not sensitive to the distance between the alkene and the functional group, including a carboxylate, on the other substituent. This observation indicates that only the double bond has to be encapsulated to effect hydrogenation. Going further, we demonstrate that this supramolecular strategy can overcome the inherent allylic alcohol selectivity of the free catalyst, achieving supramolecular catalyst-directed regioselectivity as opposed to directing-group selectivity.

Indexed as

AlkenesCatalysisHydrogenationMacromolecular SubstancesMolecular StructureOrganometallic CompoundsRhodiumAlkenesMacromolecular SubstancesOrganometallic CompoundsRhodium

Identifiers

PMID31310528
PMCPMC6756145

What OpenQuestion holds

Textmetadata
LicenceTDM
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.