Evidence map›Paper›PMID 25729560›Full record

ArticleChemical science2015

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones.

Cornelia L Boeser, Jeffrey C Holder, Buck L H Taylor, K N Houk, Brian M Stoltz, Richard N Zare

Abstract read
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In one paragraph

Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing 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

7 citing papers in PubMed.

  1. Article
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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

6 authors.

Cornelia L BoeserDepartment of Chemistry, Stanford University, Stanford, CA 94305, USA.
Jeffrey C HolderThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Buck L H TaylorDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
Brian M StoltzThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Richard N ZareDepartment of Chemistry, Stanford University, Stanford, CA 94305, USA.

Funding

Computational Investigation of Asymmetric Allylic Alkylation ReactionsF32GM106596 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI TAYLOR, BUCK · 2013 to 2015
$122k
NIGMS NIH HHS F32 GM106596
6 · The paper itself

Abstract

An asymmetric palladium-catalyzed conjugate addition reaction of arylboronic acids to enone substrates was investigated mechanistically. Desorption electrospray ionization coupled to mass spectrometry was used to identify intermediates of the catalytic cycle and delineate differences in substrate reactivity. Our findings provide evidence for the catalytic cycle proceeding through formation of an arylpalladium(II) cation, subsequent formation of an arylpalladium-enone complex, and, ultimately, formation of the new C-C bond. Reaction monitoring in both positive and negative ion modes revealed that 4-iodophenylboronic acid formed a relatively stable trimeric species under the reaction conditions.

Identifiers

PMID25729560
PMCPMC4338963

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Registered trials

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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.