Stereospecific Synthesis of Tri- and Tetrasubstituted α-Fluoroacrylates by Mizoroki-Heck Reaction

Organic Letters
Kevin RouséeXavier Pannecoucke

Abstract

Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between methyl α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quantitative yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogues of therapeutic agents with high yield.

References

May 15, 2001·Chemistry : a European Journal·A SundermannJ M Martin
Dec 26, 2001·Chemical Reviews·I P Beletskaya, A V Cheprakov
Mar 29, 2003·The Journal of Organic Chemistry·Vincenzo CalóNicola Cioffi
Sep 13, 2003·The Journal of Organic Chemistry·Qingwei YaoZhi Yang
Mar 18, 2005·Journal of Medicinal Chemistry·Pieter Van der VekenKoen Augustyns
Jul 1, 2006·American Journal of Physiology. Gastrointestinal and Liver Physiology·Hisayuki UneyamaKunio Torii
Apr 5, 2007·Organic & Biomolecular Chemistry·Samuel Couve-BonnaireXavier Pannecoucke
Jan 17, 2008·Chemical Society Reviews·David O'Hagan
Feb 10, 2011·Chemistry : a European Journal·Aditya L GottumukkalaAdriaan J Minnaard
Mar 15, 2011·Chemical Society Reviews·Grégory LandelleJean-François Paquin
Oct 1, 2011·The Journal of Organic Chemistry·Kensuke Hirotaki, Takeshi Hanamoto
Mar 20, 2012·Bioorganic & Medicinal Chemistry Letters·Wonsuk ChangMichael J Sofia
Aug 14, 2013·Chembiochem : a European Journal of Chemical Biology·Camille PierryXavier Pannecoucke
Oct 11, 2014·Chemistry : a European Journal·Kevin RouséeChristophe Hoarau
Nov 26, 2015·Organic & Biomolecular Chemistry·Kevin RouséeXavier Pannecoucke

❮ Previous
Next ❯

Citations

Jun 24, 2017·Chemistry : a European Journal·Marino Petrini
Jul 17, 2019·Nature Chemistry·Jianbo LiuMatthew S Sigman

❮ 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.

Related Papers

IARC Monographs on the Evaluation of Carcinogenic Risks to Humans
IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans
© 2021 Meta ULC. All rights reserved