Mechanistic study of asymmetric oxidative biaryl coupling: evidence for self-processing of the copper catalyst to achieve control of oxidase vs oxygenase activity.

Journal of the American Chemical Society
J Brian HewgleyMarisa C Kozlowski

Abstract

Copper(I) and copper(II) 1,5-diaza-cis-decalin complexes [(N2)Cu] are effective precatalysts for aerobic oxidative coupling of naphthol substrates. Mechanistic studies, however, reveal that these complexes are not the reactive form of the catalyst under steady-state conditions. Rather, the active catalyst forms in a presteady-state self-processing step that involves oxygenation of the naphthol substrate. The oxygenated substrate, NapHOX, serves as a cofactor that combines with the (N2)Cu complexes to achieve highly selective, steady-state oxidase reactivity (aerobic oxidative biaryl coupling).

References

Dec 26, 2001·Proceedings of the National Academy of Sciences of the United States of America·J P Klinman
Jun 5, 2003·Journal of the American Chemical Society·Carol A MulrooneyMarisa C Kozlowski
Feb 12, 2004·Chemical Reviews·Liviu M MiricaT Daniel P Stack
Feb 12, 2004·Chemical Reviews·Elizabeth A Lewis, William B Tolman
Feb 18, 2004·Accounts of Chemical Research·Minae Mure
Mar 17, 2004·Angewandte Chemie·István E MarkóChristopher J Urch
Jul 6, 2004·Archives of Biochemistry and Biophysics·Brian J BrazeauCarrie M Wilmot
Aug 18, 2004·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Lanying Q Hatcher, Kenneth D Karlin
Dec 8, 2004·Archives of Biochemistry and Biophysics·Jennifer L Dubois, Judith P Klinman
Jan 26, 2007·Organic Letters·Evan S DivirgilioMarisa C Kozlowski

❮ Previous
Next ❯

Citations

Jun 30, 2011·Chemical Reviews·Oleksandr O GrygorenkoIgor V Komarov
Jun 22, 2013·Chemical Reviews·Scott E AllenMarisa C Kozlowski
Mar 12, 2010·Journal of the American Chemical Society·Mao ChenAiwen Lei
Aug 10, 2010·Journal of the American Chemical Society·Amanda E KingShannon S Stahl
Sep 14, 2010·Journal of the American Chemical Society·Hiromichi EgamiTsutomu Katsuki
Feb 3, 2012·Journal of the American Chemical Society·Yi-Feng WangShunsuke Chiba
Apr 14, 2009·Journal of the American Chemical Society·Hiromichi Egami, Tsutomu Katsuki
Dec 4, 2009·Journal of the American Chemical Society·Jana Roithová, Petr Milko
Nov 10, 2009·The Journal of Organic Chemistry·Carol A MulrooneyMarisa C Kozlowski
Nov 10, 2009·The Journal of Organic Chemistry·Erin M O'BrienMarisa C Kozlowski
Mar 1, 2012·Organic Letters·Erin E Podlesny, Marisa C Kozlowski
Oct 23, 2009·Chemical Society Reviews·Marisa C KozlowskiElizabeth C Linton
Oct 21, 2009·Chemical Communications : Chem Comm·Lujuan YangShannon S Stahl
Feb 1, 2014·Natural Product Reports·Xu-Wen Li, Bastien Nay
Jan 7, 2016·The Journal of Organic Chemistry·Bijay ShresthaRamesh Giri
Dec 14, 2016·Journal of the American Chemical Society·Sachin NaruteDoron Pappo
Apr 2, 2015·Organic & Biomolecular Chemistry·Surendra ThapaRamesh Giri
Sep 17, 2014·Natural Product Reports·Tim WezemanKye-Simeon Masters
Sep 12, 2009·Chemistry : a European Journal·Esa T T Kumpulainen, Ari M P Koskinen
Jul 1, 2012·European Journal of Organic Chemistry·Carol A MulrooeyMarisa C Kozlowski
Aug 28, 2009·Chemistry : a European Journal·Alain GrandboisTyphène Michel
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Sep 20, 2012·Chemical Communications : Chem Comm·Koji Hirano, Masahiro Miura
Jul 16, 2013·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
Jan 30, 2013·Chemical Communications : Chem Comm·Michael Holtz-MulhollandShawn K Collins
Jul 13, 2013·Chemistry, an Asian Journal·Junji IchikawaTakeshi Fujita
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lin-Yang WuWen-Bo Liu
Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl

❮ 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.