ArticleJournal of the American Chemical Society2017
Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. It has been retracted, and should not be counted. Cited by 6 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
6 citing papers in PubMed, 40 citations in OpenAlex.
- Molecular Sculpting: A Multipurpose Tool for Expedited Access to Various Fluorinated Arenes via Photocatalytic Hydrodefluorination of Benzoates.The Journal of organic chemistry · 2023Article
- Chemodivergent CspScience advances · 2022Article
- Hydrogen-bonded nickel(I) complexes.Chemical communications (Cambridge, England) · 2021Article
- Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery.Journal of the American Chemical Society · 2020Article
- Selective C-F bond carboxylation ofChemical science · 2019Article
- Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation.Journal of the American Chemical Society · 2018Article
Corrections and comments
- Expression of concern · 2020-04-14Concerns/Issues about Image · Investigation by Company/Institution · Updated to Retraction ·
- Retraction · 2020-11-20Falsification/Fabrication of Data · Falsification/Fabrication of Image · Investigation by Company/Institution · Misconduct - Official Investigation(s) and/or Finding(s) · Misconduct by Author · Upgrade/Update of Prior Notice(s) · · Mohammed B. Khaled has institutional finding of misconduct;
- Expression of concern
- Retracted
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.
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.