Copper/ascorbic acid dyad as a catalytic system for selective aerobic oxidation of amines

Organic Letters
Jiri Srogl, Svatava Voltrova

Abstract

A new, environmentally benign system based on an ascorbic acid (vitamin C)/copper dyad is presented, which facilitates the oxidation of amines to carbonyl compounds. The oxidation utilizes aerobic oxygen as the ultimate electron scavenger, which accepts electrons in a cascade-like fashion via a Cu(+)/Cu(2+) and ascorbic/dehydroascorbic acid couple. Dehydroascorbic acid, the oxidation agent, finally oxidizes amine substrates in a selective fashion after forming a Schiff base intermediate. The selectivity as well as generality of the method is demonstrated on various substrates.

References

Feb 12, 2005·Chemistry : a European Journal·Joseph S M SamecJan-E Bäckvall
Feb 8, 2008·Angewandte Chemie·Ken SuzukiShun-Ichi Murahashi
Jul 24, 2008·Chemical Society Reviews·Shun-Ichi Murahashi, Dazhi Zhang

❮ Previous
Next ❯

Citations

Jun 22, 2013·Chemical Reviews·Scott E AllenMarisa C Kozlowski
May 13, 2010·Chemical Communications : Chem Comm·Marek MartinekJiri Srogl
Aug 13, 2011·Chemical Communications : Chem Comm·Lianghui LiuChun-Hua Yan
Jan 13, 2015·Bioorganic & Medicinal Chemistry Letters·Thomas ManningFengli Zhang
Dec 18, 2013·Journal of the American Chemical Society·Alison E Wendlandt, Shannon S Stahl
Jun 29, 2011·Journal of the American Chemical Society·Lin LiuFeimeng Zhou
Oct 5, 2016·The Journal of Organic Chemistry·Feng PengYingju Xu
Dec 17, 2009·Angewandte Chemie·Nicholas A Afagh, Andrei K Yudin
Feb 17, 2018·Critical Reviews in Food Science and Nutrition·Gal Y KreitmanGavin L Sacks
Apr 27, 2013·Angewandte Chemie·Julia R KhusnutdinovaDavid Milstein
Oct 21, 2020·Organic & Biomolecular Chemistry·Kathleen J Berger, Mark D Levin
Nov 26, 2020·Journal of the American Chemical Society·Shan TangDavid Milstein
Jun 20, 2020·Journal of the American Chemical Society·Vladislav G Lisnyak, Scott A Snyder

❮ 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.