Tandem Radical Fluoroalkylation-Cyclization: Synthesis of Tetrafluoro Imidazopyridines

Organic Letters
Julie CharpentierAntonio Togni

Abstract

A copper-catalyzed fluoroalkylation-cyclization sequence of alkenes and alkynes enables the synthesis of fluorinated tetra- and dihydroimidazopyridines in moderate to excellent yields within 1 h at 70 °C. This reaction, which is carried out using copper(I) acetate as the catalyst, makes use of a new class of functionalized tetrafluoroethyl reagents based on a hypervalent iodine scaffold.

References

Feb 16, 2006·Journal of the American Chemical Society·Sean H WiedemannRobert G Bergman
Sep 28, 2007·Mini Reviews in Medicinal Chemistry·Cécile Enguehard-Gueiffier, Alain Gueiffier
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Sep 16, 2011·Angewandte Chemie·Andrew T Parsons, Stephen L Buchwald
Jan 31, 2013·Organic & Biomolecular Chemistry·Robert CoyleFawaz Aldabbagh
Jan 11, 2014·Journal of the American Chemical Society·Ba L TranJohn F Hartwig
Aug 22, 2014·Nature Chemistry·Armido Studer, Dennis P Curran
Aug 26, 2014·Chemical Reviews·Julie CharpentierAntonio Togni
Aug 21, 2015·Topics in Current Chemistry·Natalja FrühAntonio Togni
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran

❮ Previous
Next ❯

Citations

Apr 22, 2016·The Journal of Organic Chemistry·Hiromichi EgamiYoshitaka Hamashima
Jun 18, 2019·Organic & Biomolecular Chemistry·Peng PengFan-Hong Wu

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

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.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

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.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

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.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.