Comprehensive Mechanistic Analysis of Palladium- and Nickel-Catalyzed α,β-Dehydrogenation of Carbonyls via Organozinc Intermediates.

Alexandra K Bodnar, Suzanne M Szewczyk, Yang Sun, Yifeng Chen, Anson X Huang, Timothy R Newhouse

Open access · greenAbstract read

In one paragraph

Article in The Journal of organic chemistry, 2024. 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

0.3field-weighted citation impact, top 54% of its field

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, 1 citations in OpenAlex.

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

6 authors at 1 institution in 1 country.

Alexandra K BodnarDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Suzanne M SzewczykDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Yang SunDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Yifeng ChenDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Anson X HuangDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Timothy R NewhouseDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.ORCID 0000-0001-8741-7236

Yale University · US

Funding

Synthesis of Neurologically Active Small MoleculesR01GM118614 · NIGMS · YALE UNIVERSITY · PI NEWHOUSE, TIMOTHY · 2017 to 2025

$3.1M

NIGMS NIH HHS R01 GM118614

6 · The paper itself

Abstract

Introducing degrees of unsaturation into small molecules is a central transformation in organic synthesis. A strategically useful category of this reaction type is the conversion of alkanes into alkenes for substrates with an adjacent electron-withdrawing group. An efficient strategy for this conversion has been deprotonation to form a stabilized organozinc intermediate that can be subjected to α,β-dehydrogenation through palladium or nickel catalysis. This general reactivity blueprint presents a window to uncover and understand the reactivity of Pd- and Ni-enolates. Within this context, it was determined that β-hydride elimination is slow and proceeds via concerted

Identifiers

PMID38377547

DOI10.1021/acs.joc.3c02572

PMCPMC11000628

OpenAlexW4391956439

What OpenQuestion holds

Textmetadata

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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.