Evidence map›Paper›PMID 29220183›Full record

ArticleThe Journal of organic chemistry2018

Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Scott E Denmark, Zachery D Matesich, Son T Nguyen, Selena Milicevic Sephton

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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.

Scott E DenmarkRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.ORCID 0000-0002-1099-9765
Zachery D MatesichRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.
Son T NguyenRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.
Selena Milicevic SephtonRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.

Funding

Organosilicon-Based Cross-Coupling ReactionsR01GM063167 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2002 to 2009
$2.5M
THE CYCLOADDITION CHEMISTRY OF NITROALKENESR01GM030938 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 1985 to 2007
$2.1M
CHEMISTRY OF CHIRAL PHOSPHORUS-STABILIZED CARBANIONSR01GM045532 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 1991 to 1994
–
NIGMS NIH HHS R01 GM030938NIGMS NIH HHS R01 GM045532NIGMS NIH HHS R01 GM063167
6 · The paper itself

Abstract

The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon-carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.

Identifiers

PMID29220183
PMCPMC6008792

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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.