Evidence map›Paper›PMID 27618638›Full record

ArticleJournal of the American Chemical Society2016

Catalytic Enantioselective Carbon-Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C-H Bonds.

Daniel T Ziegler, Gregory C Fu

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Article
  6. Article
  7. Article
  8. Phosphine Organocatalysis.Chemical reviews · 2018
    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

2 authors.

Daniel T ZieglerDivision of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
Gregory C FuDivision of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

Funding

DEVELOPMENT OF ENANTIOSELECTIVE NUCLEOPHILIC CATALYSTSR01GM057034 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI FU, GREGORY C · 1998 to 2013
$5.6M
Metal-Catalyzed Coupling ReactionsR37GM062871 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI FU, GREGORY C · 2010 to 2019
$5.5M
NIGMS NIH HHS R01 GM057034NIGMS NIH HHS R37 GM062871
6 · The paper itself

Abstract

Benzylic alcohols and ethers are common subunits in bioactive molecules, as well as useful intermediates in organic chemistry. In this Communication, we describe a new approach to the enantioselective synthesis of benzylic ethers through the chiral phosphine-catalyzed coupling of two readily available partners, γ-aryl-substituted alkynoates and alcohols, under mild conditions. In this process, the alkynoate partner undergoes an internal redox reaction. Specifically, the benzylic position is oxidized with good enantioselectivity, and the alkyne is reduced to the alkene.

Indexed as

Benzyl AlcoholsCatalysisEthersMolecular StructureOxidation-ReductionBenzyl AlcoholsEthers

Identifiers

PMID27618638
PMCPMC5065328

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.