Catalyst free synthesis of α-fluoro-β-hydroxy ketones/α-fluoro-ynols via electrophilic fluorination of tertiary propargyl alcohols using Selectfluor™ (F-TEDA-BF4)

Organic & Biomolecular Chemistry
Naganaboina Naveen, Rengarajan Balamurugan


A facile method for the synthesis of α-fluoro-β-hydroxy ketones/α-fluoro-ynols from tertiary propargyl alcohols under electrophilic fluorination conditions using F-TEDA-BF4 has been presented. The products bear pharmaceutically important α-fluoro ketone, gem-diaryl and fluorohydrin moieties in the same molecule. Interestingly, this catalyst free protocol results in monofluorination.


Nov 1, 1984·Journal of Medicinal Chemistry·W M WelchB K Koe
May 30, 1997·European Journal of Pharmacology·L NilvebrantB Sparf
Apr 1, 2000·Bioorganic & Medicinal Chemistry Letters·C G BelloC Abell
Aug 2, 2000·Proceedings of the National Academy of Sciences of the United States of America·M E Phelps
Mar 27, 2001·Annual Review of Pharmacology and Toxicology·B K ParkP M O'Neill
May 29, 2002·Bioorganic & Medicinal Chemistry Letters·R P AlexanderG Higgs
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Peter Jeschke
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Hans-Joachim BöhmMartin Stahl
Apr 1, 1994·Natural Product Reports·D B Harper, D O'Hagan
Dec 4, 2004·Angewandte Chemie·Paul T NyffelerChi-Huey Wong
Mar 25, 2005·Organic Letters·Ma Carmen Pacheco, Véronique Gouverneur
Jul 2, 2005·The Journal of Organic Chemistry·Weimin Peng, Jean'ne M Shreeve
Aug 25, 2005·Journal of the American Chemical Society·Pramod K MohantaRobert A Flowers
Dec 19, 2006·Bioorganic & Medicinal Chemistry Letters·Claire L ArthursIan J Stratford
Sep 29, 2007·Science·Klaus MüllerFrançois Diederich
Jan 17, 2008·Chemical Society Reviews·David O'Hagan
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Apr 23, 2008·Chemical Reviews·Simon M AmetameyPius August Schubiger
Sep 24, 2008·The Journal of Organic Chemistry·Kyu-Young KimHyunik Shin
May 2, 2009·Drugs·Kate McKeage, Gillian M Keating
Feb 19, 2010·Journal of the American Chemical Society·Julia A Kalow, Abigail G Doyle
Apr 23, 2010·Organic Letters·Roy M MalamakalTodd A Davis
May 27, 2010·Beilstein Journal of Organic Chemistry·Luke Hunter
Jul 1, 2010·Chemical Communications : Chem Comm·Teresa de Haro, Cristina Nevado
Aug 1, 2009·Future Medicinal Chemistry·Robert Filler, Rituparna Saha
Aug 26, 2011·Journal of the American Chemical Society·Julia A Kalow, Abigail G Doyle
Jan 4, 2012·Angewandte Chemie·Ryan Littich, Peter J H Scott
Feb 16, 2012·Chemical Communications : Chem Comm·Charlotte Hollingworth, Véronique Gouverneur
Feb 23, 2013·Journal of Medicinal Chemistry·Changho HanDavid A Colby
Jun 20, 2013·Angewandte Chemie·Peng Zhang, Christian Wolf
Jun 26, 2013·The Journal of Organic Chemistry·Wioleta BorzęckaVicente Gotor
Jul 23, 2013·Angewandte Chemie·Theresa LiangTobias Ritter

Related Concepts

Trending Feeds


Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Hereditary Sensory Autonomic Neuropathy

Hereditary Sensory Autonomic Neuropathies are a group of inherited neurodegenerative disorders characterized clinically by loss of sensation and autonomic dysfunction. Here is the latest research on these neuropathies.

Spatio-Temporal Regulation of DNA Repair

DNA repair is a complex process regulated by several different classes of enzymes, including ligases, endonucleases, and polymerases. This feed focuses on the spatial and temporal regulation that accompanies DNA damage signaling and repair enzymes and processes.

Glut1 Deficiency

Glut1 deficiency, an autosomal dominant, genetic metabolic disorder associated with a deficiency of GLUT1, the protein that transports glucose across the blood brain barrier, is characterized by mental and motor developmental delays and infantile seizures. Follow the latest research on Glut1 deficiency with this feed.

Separation Anxiety

Separation anxiety is a type of anxiety disorder that involves excessive distress and anxiety with separation. This may include separation from places or people to which they have a strong emotional connection with. It often affects children more than adults. Here is the latest research on separation anxiety.

KIF1A Associated Neurological Disorder

KIF1A associated neurological disorder (KAND) is a rare neurodegenerative condition caused by mutations in the KIF1A gene. KAND may present with a wide range and severity of symptoms including stiff or weak leg muscles, low muscle tone, a lack of muscle coordination and balance, and intellectual disability. Find the latest research on KAND here.

Regulation of Vocal-Motor Plasticity

Dopaminergic projections to the basal ganglia and nucleus accumbens shape the learning and plasticity of motivated behaviors across species including the regulation of vocal-motor plasticity and performance in songbirds. Discover the latest research on the regulation of vocal-motor plasticity here.