Evidence map›Paper›PMID 33661619›Full record

ArticleJournal of the American Chemical Society2021

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis.

Teng Yuan, Qi Tang, Chuan Shan, Xiaohan Ye, Jin Wang, Pengyi Zhao, Lukasz Wojtas, Nicholas Hadler, Hao Chen, Xiaodong Shi

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. 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
4.6field-weighted citation impact, top 4% 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

8 citing papers in PubMed, 54 citations in OpenAlex.

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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

10 authors at 3 institutions in 2 countries.

Teng YuanDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Qi TangDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Chuan ShanDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Xiaohan YeDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Jin WangCollege of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong 250014, China.
Pengyi ZhaoDepartment of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, New Jersey 07102, United States.ORCID 0000-0002-7873-1773
Lukasz WojtasDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Nicholas HadlerDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.
Hao ChenDepartment of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, New Jersey 07102, United States.ORCID 0000-0001-8090-8593
Xiaodong ShiDepartment of Chemistry, University of South Florida, Tampa, Florida 33620, United States.ORCID 0000-0002-3189-1315
University of South Florida · USNew Jersey Institute of Technology · USShandong Normal University · CN

Funding

Achieving challenging coupling with gold redox catalysisR01GM120240 · NIGMS · UNIVERSITY OF SOUTH FLORIDA · PI SHI, XIAODONG · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM120240
6 · The paper itself

Abstract

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Indexed as

AlkynesCatalysisDiazonium CompoundsGoldOxidation-ReductionQuantum TheoryTemperatureVinyl CompoundsAlkynesDiazonium CompoundsGoldVinyl Compounds

Identifiers

PMID33661619
PMCPMC10270734
OpenAlexW3134537919

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

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.