Anodic Olefin Coupling Reactions: Elucidating Radical Cation Mechanisms and the Interplay between Cyclization and Second Oxidation Steps.

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Zach Medcalf, Kevin D Moeller

Abstract

Anodic olefin coupling reactions generate new bonds and ring skeletons through a net two electron process that reverses the polarity of a known, electron-rich functional group. While much of the early work on the mechanism of these reactions focused on the initial oxidation and cyclization steps of the process, the second oxidation step also plays a central role in determining the success of the reaction. Evidence supporting this observation is presented, along with evidence that optimization of this second oxidation step is not enough to pull a poor cyclization to the desired product. Successful cyclization reactions require optimization of both processes.

References

Mar 8, 1996·The Journal of Organic Chemistry·Dallas G. NewKevin D. Moeller
Oct 25, 2001·The Journal of Organic Chemistry·Michael SchmittelRolf Söllner
Sep 26, 2003·Organic Letters·David CrichSochanchingwung Rumthao
Jul 22, 2004·Journal of the American Chemical Society·John Mihelcic, Kevin D Moeller
Jul 29, 2005·Organic Letters·Chambers C HughesDirk Trauner
Jun 23, 2006·Chemical Society Reviews·Jeffrey B Sperry, Dennis L Wright
Dec 21, 2006·Journal of the American Chemical Society·Aubry K MillerDirk Trauner
May 15, 2007·Journal of the American Chemical Society·Hye-Young JangDavid W C MacMillan
Sep 27, 2007·Journal of the American Chemical Society·Feili Tang, Kevin D Moeller
Jun 21, 2008·Chemical Reviews·Jun-ichi YoshidaAiichiro Nagaki
Aug 8, 2008·Angewandte Chemie·Michael E GreenPaul E Floreancig
Dec 5, 2008·Organic Letters·Christopher T AvettaRegan J Thomson
Jun 26, 2009·Organic Letters·Lei Liu, Paul E Floreancig
Nov 6, 2009·Organic Letters·Leah C KonkolRegan J Thomson
Mar 26, 2010·Journal of the American Chemical Society·Sebastian Rendler, David W C Macmillan
Jun 10, 2010·Journal of the American Chemical Society·Michael A IschayTehshik P Yoon
Jul 3, 2010·Journal of the American Chemical Society·Nathan T JuiDavid W C MacMillan
Jul 16, 2010·Angewandte Chemie·James J DeveryRobert A Flowers
Mar 8, 2011·Organic Letters·Alison Redden, Kevin D Moeller
Mar 9, 2013·European Journal of Organic Chemistry·Fenghai GuoRegan J Thomson
Jul 3, 2013·Journal of the American Chemical Society·Andrew J Perkowski, David A Nicewicz
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Jie HuNan Zheng
Feb 7, 2014·Chemical Society Reviews·Robert Francke, R Daniel Little
Jun 24, 2017·Chemical Reviews·Hong YiAiwen Lei
Sep 1, 2017·Accounts of Chemical Research·Ruozhu FengKevin D Moeller
Jan 24, 2018·Angewandte Chemie·Sabine MöhleSiegfried R Waldvogel

❮ Previous
Next ❯

Citations

Oct 8, 2021·The Journal of Organic Chemistry·Ruby Krueger, Kevin D Moeller

❮ 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.