Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

Chemistry : a European Journal
M HartmannArmido Studer

Abstract

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

References

Apr 27, 2001·Chemistry : a European Journal·A Studer
Apr 5, 2005·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Armido Studer, Tobias Schulte
Jul 14, 2006·Organic Letters·Markus R HeinrichSabrina Wölfel
Jan 16, 2007·The Journal of Organic Chemistry·Markus R HeinrichAlexander Wetzel
Nov 15, 2007·The Journal of Organic Chemistry·Markus R HeinrichMarcel Kirschstein
Feb 9, 2008·Organic Letters·Christian PerreaultAndré B Charette
May 29, 2008·The Journal of Organic Chemistry·Marcin BielawskiBerit Olofsson
Nov 27, 2008·The Journal of Organic Chemistry·Sébastien R GoudreauAndré B Charette
Dec 17, 2009·Organic Letters·Stefano NicolaiJérôme Waser
Mar 4, 2011·Journal of Computational Chemistry·Stefan GrimmeLars Goerigk
Mar 9, 2011·Chemistry : a European Journal·Tsuyoshi TaniguchiHiroyuki Ishibashi
May 4, 2011·Angewandte Chemie·Ludger Tebben, Armido Studer
Jul 27, 2012·Angewandte Chemie·Yi Li, Armido Studer
Sep 27, 2012·Journal of the American Chemical Society·Marcel HartmannArmido Studer
Jan 30, 2013·Organic & Biomolecular Chemistry·Fanyang MoJianbo Wang
Apr 12, 2013·Angewandte Chemie·Durga Prasad Hari, Burkhard König
Jun 19, 2013·Organic Letters·Donald R Wenz, Javier Read de Alaniz
Jun 20, 2013·Journal of the American Chemical Society·Reto Frei, Jérôme Waser
Aug 13, 2013·Organic Letters·Bo Zhang, Armido Studer
Sep 17, 2013·Angewandte Chemie·Simon Breitler, Erick M Carreira
Feb 15, 2014·The Journal of Organic Chemistry·Josefa HofmannMarkus R Heinrich
Mar 7, 2014·Journal of the American Chemical Society·Fang XieXingwei Li
Jun 7, 2014·Journal of the American Chemical Society·Fengzhi ZhangMatthew J Gaunt
Jul 22, 2014·Angewandte Chemie·Marcel Hartmann, Armido Studer
Jul 22, 2014·Angewandte Chemie·Alexander S IvanovViktor V Zhdankin
Aug 26, 2014·Chemical Reviews·Julie CharpentierAntonio Togni
Nov 20, 2014·Organic & Biomolecular Chemistry·Yao-Feng WangFu-Xue Chen
Jan 15, 2015·The Journal of Organic Chemistry·Yunxiang WuYuanchao Li
Jan 20, 2015·Chemical Communications : Chem Comm·Marcel HartmannArmido Studer
Jan 31, 2015·Organic Letters·C Chun Chen, Jerome Waser

❮ Previous
Next ❯

Citations

Jun 22, 2017·Accounts of Chemical Research·Xi Wang, Armido Studer
Aug 10, 2017·Chemistry : a European Journal·David R Stuart
Apr 15, 2018·Chemistry : a European Journal·Mohamed Elsherbini, Thomas Wirth
Dec 5, 2018·Chemistry : a European Journal·Narumi KomamiShigeki Matsunaga
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
Jun 9, 2016·Angewandte Chemie·Stephanie KindtMarkus R Heinrich
Jul 27, 2017·Chemical Communications : Chem Comm·Jason TaoGraham K Murphy
Dec 15, 2020·Chemical Society Reviews·Nikita Kvasovs, Vladimir Gevorgyan
Jun 8, 2021·Chemical Science·Timothée ConstantinDaniele Leonori
May 10, 2018·Journal of the American Chemical Society·Ying ChengArmido Studer
Jul 1, 2020·The Journal of Physical Chemistry Letters·Elena MiliutinaPavel S Postnikov

❮ 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.