ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Palladium-Catalyzed C(sp
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 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
12 citing papers in PubMed.
- Selective C-H Activation of Unprotected Allylamines by Control of Catalyst Speciation.Chem catalysis · 2023Article
- Dual Copper- and Aldehyde-Catalyzed Transient C-H Sulfonylation of Benzylamines.Organic letters · 2023Article
- Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.RSC advances · 2022Article
- Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.Chemical science · 2022Article
- Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups.Angewandte Chemie (International ed. in English) · 2022Article
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Aldehyde catalysis - from simple aldehydes to artificial enzymes.RSC advances · 2020Review
- Pd-Catalyzed γ-C(spJournal of the American Chemical Society · 2020Article
- Transient Directing Group Enabled Pd-catalyzed γ-C(spACS catalysis · 2020Article
- Palladium-Catalyzed C(spChemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
C-H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C-H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C-H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ϵ-cyclopalladation of the arylation product is reported.
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.