ArticleNature communications2017
A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.
Article in Nature communications, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 78 citations in OpenAlex.
- Nickel-Catalyzed α‑Arylation and Alkenylation of α‑Trifluoromethyl Amines via 1,2-HAT Assisted by DMSO.JACS Au · 2026Article
- Hydrolytic instability of C-F bonds in 2,2,2-trifluoroethyl-phosphinic acid systems: formation of carboxymethylphosphinic acid derivatives.RSC advances · 2025Article
- Cobalt-catalyzed reductive cross-coupling: a review.Molecular diversity · 2025Review
- Electroreductive amination of carboxylic acids by cobalt catalysis.Nature communications · 2025Article
- TiFRSC advances · 2024Article
- Reactivity-based identification of oxygen containing functional groups of chemicals applied as potential classifier in non-target analysis.Scientific reports · 2023Article
- Iron porphyrin-catalyzedRSC advances · 2021Article
- A practical catalytic reductive amination of carboxylic acids.Chemical science · 2020Article
- Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.Nature communications · 2019Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Amines are a fundamentally important class of biologically active compounds and the ability to manipulate their physicochemical properties through the introduction of fluorine is of paramount importance in medicinal chemistry. Current synthesis methods for the construction of fluorinated amines rely on air and moisture sensitive reagents that require special handling or harsh reductants that limit functionality. Here we report practical, catalyst-free, reductive trifluoroethylation reactions of free amines exhibiting remarkable functional group tolerance. The reactions proceed in conventional glassware without rigorous exclusion of either moisture or oxygen, and use trifluoroacetic acid as a stable and inexpensive fluorine source. The new methods provide access to a wide range of medicinally relevant functionalized tertiary β-fluoroalkylamine cores, either through direct trifluoroethylation of secondary amines or via a three-component coupling of primary amines, aldehydes and trifluoroacetic acid. A reduction of in situ-generated silyl ester species is proposed to account for the reductive selectivity observed.
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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.