Base-Free Pd-Catalyzed C-Cl Borylation of Fluorinated Aryl Chlorides.

Chemistry : a European Journal
Yudha P BudimanTodd B Marder

Abstract

Catalytic C-X borylation of aryl halides containing two ortho-fluorines has been found to be challenging, as most previous methods require stoichiometric amounts of base and the polyfluorinated aryl boronates suffer from protodeboronation, which is accelerated by ortho-fluorine substituents. Herein, we report that a combination of Pd(dba)2 (dba=dibenzylideneacetone) with SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) as a ligand is efficient to catalyze the C-Cl borylation of aryl chlorides containing two ortho-fluorine substituents. This method, conducted under base-free conditions, is compatible with the resulting di-ortho-fluorinated aryl boronate products which are sensitive to base.

References

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
Feb 28, 2007·Chemical Communications : Chem Comm·Francesco BabudriRoberta Ragni
Sep 29, 2007·Science·Klaus MüllerFrançois Diederich
Jun 24, 2008·Journal of Medicinal Chemistry·William K Hagmann
Aug 25, 2009·Pest Management Science·Peter Jeschke
Mar 31, 2011·Chemical Society Reviews·Ricarda BergerJürg Hulliger
Jul 10, 2012·Journal of the American Chemical Society·Gary A MolanderMatthew T Tudge
Apr 15, 2014·Chemistry : a European Journal·Hélène D S GuerrandMathieu Pucheault
May 16, 2014·The Journal of Organic Chemistry·Jerome LozadaDavid M Perrin
Nov 25, 2014·Organic Letters·Chathurika R K JayasundaraRobert E Maleczka
Sep 16, 2015·Journal of the American Chemical Society·Takayuki FurukawaNaoto Chatani
Sep 22, 2015·Angewandte Chemie·Shubhankar Kumar BoseTodd B Marder
Oct 6, 2015·Chemical Communications : Chem Comm·Jun TakayaNobuharu Iwasawa
Dec 21, 2016·Journal of the American Chemical Society·Li Zhang, Lei Jiao
Jun 22, 2019·Organic & Biomolecular Chemistry·Laura KuehnTodd B Marder

❮ Previous
Next ❯

Citations


❮ 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.