ArticleChemical science2022
Hydroarylation of enamides enabled by HFIP
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 33 citations in OpenAlex.
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- Challenging the Bredt's rule in an acid catalyzed cationic cyclization to get bicyclo[3.3.1]nonane derivatives.Nature communications · 2025Article
- Hexafluoroisopropanol-Mediated Cascade Cyclization for Construction of α‑Amino-γ-spirolactones.JACS Au · 2025Article
- Aliphatic Amines Unlocked for Selective Transformations through Diazotization.Angewandte Chemie (International ed. in English) · 2025Article
- Stereospecific Synthesis of Unprotected, α,β-Disubstituted Tryptamines and Phenethylamines from 1,2-Disubstituted Alkenes via a One-Pot Reaction Sequence.Organic letters · 2023Article
- Development of a Non-Directed Petasis-Type Reaction by an Aromaticity-Disrupting Strategy.Angewandte Chemie (International ed. in English) · 2023Article
- Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles.Angewandte Chemie (International ed. in English) · 2022Article
- Oxidative bridgehead functionalization of (4 + 3) cycloadducts obtained from oxidopyridinium ions.RSC advances · 2022Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Here we describe that HFIP greatly expands the scope with respect to both reaction partners of the Brønsted acid-catalyzed hydroarylation of enamides. The reaction is fast and practical and can be performed on the gram scale. A hexafluoroisopropyl ether intermediate was isolated from the reaction mixture and was shown to convert to the product when resubmitted to the reaction conditions. Extensive kinetic studies and computations reveal that the hexafluoroisopropyl ether is formed rapidly and serves as a slow-release reservoir for the key cationic intermediate, preventing the oligomerization of the substrate under the reaction conditions. Given the relatively low electrophilicity of the cationic intermediates in the present study, it seems likely that HFIP also actively participates in other reactions involving more electrophilic carbocations.
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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.