ArticleAngewandte Chemie (International ed. in English)2020
Photoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 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
16 citing papers in PubMed, 125 citations in OpenAlex.
- Merging photocatalysis with C-H insertions enabled switchable synthesis of indoles and indolines.Nature communications · 2026Article
- Synthesis of Unsymmetrical Dialkyl Ethers via Direct Etherification Cocatalyzed Using FeClACS omega · 2026Article
- Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.JACS Au · 2025Article
- Further Mechanistic Investigations into the Blue Light-Driven O-H Functionalization of Alcohols by Aryldiazoacetates.The Journal of organic chemistry · 2025Article
- Photochemical Functionalization of 4‑Diazoisoquinoline-1,3(2ACS organic & inorganic Au · 2025Article
- Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions.ACS central science · 2025Article
- Hexafluoroisopropanol Solvent Effects on Enantioselectivity of Dirhodium Tetracarboxylate-Catalyzed Cyclopropanation.Journal of the American Chemical Society · 2025Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Article
- Visible-light-induced organocatalytic enantioselective N-H insertion of α-diazoesters enabled by indirect free carbene capture.Chemical science · 2023Article
- Hydrogen Bonding Networks Enable Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis.Angewandte Chemie (International ed. in English) · 2022Article
- Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Photocatalytic gem-Difluoroolefination Reactions by a Formal C-C Coupling/Defluorination Reaction with Diazoacetates.Angewandte Chemie (International ed. in English) · 2022Article
- Asymmetric synthesis of pharmaceutically relevant 1-aryl-2-heteroaryl- and 1,2-diheteroarylcyclopropane-1-carboxylates.Chemical science · 2021Article
- Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes-Experiment and Theory*.Angewandte Chemie (International ed. in English) · 2021Article
- Photoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Hexafluoroisopropanol is typically considered as an unreactive solvent and not as a reagent in organic synthesis. Herein, we report on a mild and efficient photochemical reaction of aryl diazoacetates with hexafluoroisopropanol that enables, under stoichiometric reaction conditions, the synthesis of fluorinated ethers in excellent yield. Mechanistic studies indicate there is a preorganization of hexafluoroisopropanol and the diazoalkane acts as an unreactive hydrogen-bonding complex. Only after photoexcitation does this complex undergo a protonation-substitution reaction to the reaction product. Investigations on the applicability of this photochemical transformation show that a broad variety of acidic alcohols can be subjected to this transformation and thus demonstrate the feasibility of this concept for O-H functionalization reactions (54 examples, up to 98 % yield).
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.