Efficient and selective Cu/nitroxyl-catalyzed methods for aerobic oxidative lactonization of diols

Journal of the American Chemical Society
Xiaomin Xie, Shannon S Stahl

Abstract

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

References

Oct 25, 2001·The Journal of Organic Chemistry·Takahiro NishimuraSakae Uemura
Apr 14, 2005·Journal of the American Chemical Society·Hideki ShimizuTsutomu Katsuki
Aug 28, 2007·Chemical Society Reviews·Charlotte K Williams
Sep 12, 2009·Chemistry : a European Journal·Esa T T Kumpulainen, Ari M P Koskinen
Dec 15, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kiyotomi KanedaKoichiro Jitsukawa
Dec 25, 2010·Chemical Communications : Chem Comm·Masato ItoTakao Ikariya
Aug 25, 2011·Journal of the American Chemical Society·Jessica M Hoover, Shannon S Stahl
Oct 1, 2011·Chemistry : a European Journal·Yoshinori Endo, Jan-E Bäckvall
Jan 16, 2013·Journal of the American Chemical Society·Jessica M HooverShannon S Stahl
May 11, 2013·Journal of the American Chemical Society·Kevin ChungRobert M Waymouth
Oct 17, 2013·Journal of the American Chemical Society·Janelle E Steves, Shannon S Stahl
Feb 21, 2014·Angewandte Chemie·Yusuke SasanoYoshiharu Iwabuchi
Mar 29, 2014·Chemical Communications : Chem Comm·Qun CaoMark J Muldoon
Jun 20, 2014·Journal of the American Chemical Society·Timothy R Blake, Robert M Waymouth
Aug 5, 2014·Journal of the American Chemical Society·Bradford L RylandShannon S Stahl

❮ Previous
Next ❯

Citations

Oct 28, 2015·Journal of the American Chemical Society·Mohammad RafieeShannon S Stahl
May 14, 2016·Journal of the American Chemical Society·Susan L ZultanskiShannon S Stahl
Mar 11, 2017·Organic & Biomolecular Chemistry·Shelli A MillerNicholas E Leadbeater
Apr 1, 2018·ChemMedChem·Pankaj Kumar Singh, Om Silakari
Apr 25, 2019·Angewandte Chemie·Hidde ElferinkThomas J Boltje
Sep 15, 2020·Chemical Communications : Chem Comm·Andrea Chaves-PousoMartín Fañanás-Mastral
Nov 4, 2017·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Emiko WadaHisao Yoshida
Apr 4, 2021·International Journal of Molecular Sciences·Joonseong HurJaehoon Sim
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Larisa N Grigor'evaDmitrii G Mazhukin
Feb 20, 2020·Chemical Science·Timothy R BlakeRobert M Waymouth
Jun 6, 2017·Journal of the American Chemical Society·Kevin B Smith, M Kevin Brown
Dec 16, 2017·Journal of the American Chemical Society·Wilson C HoRobert M Waymouth
Aug 8, 2018·Journal of the American Chemical Society·Xuesong WuVy M Dong
Feb 19, 2020·The Journal of Organic Chemistry·Jean-François ParentPierre Deslongchamps
Dec 11, 2019·The Journal of Organic Chemistry·Jean-François ParentPierre Deslongchamps
Dec 9, 2020·The Journal of Organic Chemistry·Alankrita GariaNidhi Jain
Dec 8, 2017·Organic Letters·Sheng ZhangChengchu Zeng
Jul 10, 2019·Organic Letters·Ierasia TriandafillidiChristoforos G Kokotos

❮ 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.