Regioselective iron-catalyzed decarboxylative allylic etherification

Organic Letters
Rushi Trivedi, Jon A Tunge

Abstract

An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through pi-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via sigma-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.

References

Sep 23, 2003·Angewandte Chemie·K C NicolaouAndreas Ritzén
Jul 17, 2004·Organic Letters·Erin C Burger, Jon A Tunge
Jun 2, 2005·Chemical Communications : Chem Comm·Erin C Burger, Jon A Tunge
Sep 30, 2005·Journal of the American Chemical Society·Dinesh Kumar Rayabarapu, Jon A Tunge
Jan 28, 2006·Angewandte Chemie·Bernd Plietker
Aug 10, 2006·Angewandte Chemie·Bernd Plietker
Mar 21, 2007·Journal of the American Chemical Society·Shelli R Waetzig, Jon A Tunge
May 23, 2008·Chemistry : a European Journal·Martina AusteriJérôme Lacour
Sep 13, 2008·Organic Letters·Jimmie D Weaver, Jon A Tunge
May 23, 2009·Tetrahedron·K C NicolaouChristine F Gelin

❮ Previous
Next ❯

Citations

Jan 18, 2011·Chemical Reviews·Jimmie D WeaverJon A Tunge
Aug 13, 2011·Journal of the American Chemical Society·Alexander J Grenning, Jon A Tunge
Dec 15, 2016·Organic & Biomolecular Chemistry·Pradeep KumarNamrata Dwivedi
May 17, 2018·Chemistry, an Asian Journal·Liang GeHongli Bao
Jul 17, 2019·Chemistry, an Asian Journal·Aslihan BaykalBernd Plietker
Mar 12, 2011·Organic Letters·Gopala K Jarugumilli, Silas P Cook
Mar 10, 2015·Chemical Reviews·Ingmar Bauer, Hans-Joachim Knölker
Jul 26, 2014·Journal of the American Chemical Society·Alexander J GrenningJohn A Porco
Sep 16, 2011·Organic Letters·André P Dieskau, Bernd Plietker
Nov 21, 2017·Organic Letters·Jianing XieArjan W Kleij
Nov 20, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Sourav KunduAlakesh Bisai

❮ 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.