ArticleChemical science2020
Stereoselective synthesis of pentasubstituted 1,3-dienes
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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.
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.
Who cites it
11 citing papers in PubMed, 50 citations in OpenAlex.
- Alkyne dimerization-hydroarylation to form pentasubstituted 1,3-dienes via binuclear nickel catalysis.Nature communications · 2025Article
- Dienes as Versatile Substrates for Transition Metal-Catalyzed Reactions.Angewandte Chemie (International ed. in English) · 2024Review
- Nickel-catalyzed electrophiles-controlled enantioselective reductive arylative cyclization and enantiospecific reductive alkylative cyclization of 1,6-enynes.Nature communications · 2024Article
- Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes.Organic letters · 2023Article
- Mechanistic Versatility at Ir(PSiP) Pincer Catalysts: Triflate Proton Shuttling from 2-Butyne to Diene and [3]Dendralene Motifs.Organometallics · 2022Article
- Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes.Molecules (Basel, Switzerland) · 2022Article
- Rapid access toChemical science · 2022Article
- Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-Yne-Ene Coupling Reaction.Angewandte Chemie (International ed. in English) · 2022Article
- Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol.Chemical science · 2021Article
- Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The reductive coupling of alkynes represents a powerful strategy for the rapid synthesis of highly substituted 1,3-dienes. This method has the advantages of high atom and step economy, and readily available substrates. Unfortunately, the intermolecular coupling of unsymmetrical internal alkynes remains extremely challenging due to the difficulty in controlling self-dimerization and cross-coupling, as well as stereo- and regioselectivity. Previous reports are still limited to intramolecular processes or the use of stoichiometric amounts of metal catalyst. Herein, we report that nickel-catalyzed reductive coupling of two unsymmetrical internal alkynes can overcome the above-mentioned limitations by using a hemilabile directing group strategy to control the regioselectivity. A series of synthetically challenging penta-substituted 1,3-dienes are obtained in good yields with high regio- and enantioselectivity (mostly > 20/1 rr, >90% ee).
Identifiers
What OpenQuestion holds
Registered trials
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.