Evidence map›Paper›PMID 37920349›Full record

ArticleChemical science2023

Rearrangement of a carboxy-substituted spiro[4.4]nonatriene to annulated fulvenes through a Pd(ii)-mediated 1,5-vinyl shift.

Karan Goyal, Garrett A Kukier, Xiangyang Chen, Aneta Turlik, K N Houk, Richmond Sarpong

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2023. 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

6 authors.

Karan GoyalDepartment of Chemistry, University of California Berkeley CA 94720 USA rsarpong@berkeley.edu.
Garrett A KukierDepartment of Chemistry and Biochemistry, University of California Los Angeles CA 90095 USA houk@chem.ucla.edu.
Xiangyang ChenDepartment of Chemistry and Biochemistry, University of California Los Angeles CA 90095 USA houk@chem.ucla.edu.
Aneta TurlikDepartment of Chemistry and Biochemistry, University of California Los Angeles CA 90095 USA houk@chem.ucla.edu.
K N HoukDepartment of Chemistry and Biochemistry, University of California Los Angeles CA 90095 USA houk@chem.ucla.edu.ORCID https://orcid.org/0000-0002-8387-5261
Richmond SarpongDepartment of Chemistry, University of California Berkeley CA 94720 USA rsarpong@berkeley.edu.ORCID https://orcid.org/0000-0002-0028-6323

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026
$5.4M
A proposal for the purchase of a new Cu anode Microsource X-ray Diffractometer wiS10RR027172 · NCRR · UNIVERSITY OF CALIFORNIA BERKELEY · PI RAYMOND, KENNETH N · 2010 to 2010
$500k
High Performance Computing Cluster for Public Health Driven Molecular Science - Core FacilityS10OD023532 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI DURKIN, KATHLEEN A · 2017 to 2017
$434k
Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, BerkeleyS10OD024998 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI HARTWIG, JOHN F · 2018 to 2018
$265k
Computational Investigations of Asymmetric Carbon-Carbon Bond FormationF32GM134709 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI TURLIK, ANETA · 2021 to 2022
$90k
NCRR NIH HHS S10 RR027172NIGMS NIH HHS F32 GM134709NIGMS NIH HHS R35 GM130345NIH HHS S10 OD023532NIH HHS S10 OD024998
6 · The paper itself

Abstract

A novel synthesis of aryl-substituted, enantioenriched fulvenes from an oxidative Heck cascade and rearrangement of a carboxy-substituted spiro[4.4]nonatriene is disclosed. Mechanistic investigations with density functional theory (DFT) calculations and empirical results support the net transformation occurring through a novel Pd(ii)-mediated 1,5-vinyl shift from a vinyl-palladium intermediate that terminates with protodepalladation. This spiro-to-fused bicycle conversion tolerates a range of electron-rich and deficient arylboronic acids to give a range of mono- and diaryl substituted annulated fulvenes in moderate to good yields and enantiomeric ratios. Overall, this work connects two classes of molecules with a rich history in physical organic chemistry.

Identifiers

PMID37920349
PMCPMC10619539

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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.