ArticleAngewandte Chemie (International ed. in English)2021
Catalyst-Controlled Regiodivergent C-H Alkynylation of Thiophenes*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 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
17 citing papers in PubMed, 46 citations in OpenAlex.
- Catalyst-Controlled Regiodivergent C-H Olefination of Furanyl Carbamates through a Rational Approach.JACS Au · 2026Article
- Elucidating Ligand-Dependent Selectivities in Pd-Catalyzed C-H Activations.Angewandte Chemie (International ed. in English) · 2025Article
- Palladium-Catalyzed Non-Directed C─H Functionalization of Arenes with Trifluoromethylated Olefins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Electrocatalyzed direct arene alkenylations without directing groups for selective late-stage drug diversification.Nature communications · 2023Article
- Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.Chemical reviews · 2023Review
- Sterically controlled isodesmic late-stage C-H iodination of arenes.Chemical science · 2023Article
- Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C-H olefination of aromatic compounds.Chemical science · 2023Article
- Silver-Free C-H Activation: Strategic Approaches towards Realizing the Full Potential of C-H Activation in Sustainable Organic Synthesis.Angewandte Chemie (International ed. in English) · 2022Review
- Site-Selective C-H Arylation of Diverse Arenes Ortho to Small Alkyl Groups.Angewandte Chemie (International ed. in English) · 2022Article
- Selective Para-C-H Alkynylation of Aniline Derivatives by Pd/S,O-Ligand Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Site-Selective Pd-Catalyzed C(spChemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Rhodium-catalysedChemical science · 2021Article
- Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.Journal of the American Chemical Society · 2021Article
- Ligand switchable site selectivity in C-H alkenylation of thiophenes by turnover-limiting step control.Chemical communications (Cambridge, England) · 2021Article
- Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives.RSC advances · 2021Article
- Mechanism of the Arene-Limited Nondirected C-H Activation of Arenes with Palladium*.Angewandte Chemie (International ed. in English) · 2021Article
- Catalyst-Controlled Regiodivergent C-H Alkynylation of Thiophenes*.Angewandte Chemie (International ed. in English) · 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
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkynes are highly attractive motifs in organic synthesis due to their presence in natural products and bioactive molecules as well as their versatility in a plethora of subsequent transformations. A common procedure to insert alkynes into (hetero)arenes, such as the thiophenes studied herein, consists of a halogenation followed by a Sonogashira cross-coupling. The regioselectivity of this approach depends entirely on the halogenation step. Similarly, direct alkynylations of thiophenes have been described that follow the same regioselectivity patterns. Herein we report the development of a palladium catalyzed C-H activation/alkynylation of thiophenes. The method is applicable to a broad range of thiophene substrates. For 3-substituted substrates where controlling the regioselectivity between the C2 and C5 position is particularly challenging, two sets of reaction conditions enable a regiodivergent reaction, giving access to each regioisomer selectively. Both protocols use the thiophene as limiting reagent and show a broad scope, rendering our method suitable for late-stage modification.
Indexed as
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.