Clean and efficient benzylic C-H oxidation in water using a hypervalent iodine reagent: activation of polymeric iodosobenzene with KBr in the presence of montmorillonite-K10

The Journal of Organic Chemistry
Toshifumi DohiYasuyuki Kita

Abstract

We have found that unreactive and insoluble polymeric iodosobenzene [PhIO] n induced aqueous benzylic C-H oxidation to effectively give arylketones, in the presence of KBr and montmorillonite-K10 (M-K10) clay. Water-soluble and reactive species 1 having the unique I(III)-Br bond, in situ generated from [PhIO]n and KBr, was considered to be the key radical initiator during the reactions.

References

May 9, 1996·Chemical Reviews·Peter J. Stang, Viktor V. Zhdankin
Feb 20, 2002·Chemical Reviews·Noritaka Mizuno, Makoto Misono
Jul 11, 2002·Chemical Reviews·Viktor V Zhdankin, Peter J Stang
Aug 15, 2002·Chemical Reviews·Ulf M Lindström
Apr 13, 2005·The Journal of Organic Chemistry·Robert M Moriarty
Apr 14, 2005·Angewandte Chemie·Thomas Wirth
May 12, 2005·Chemical Communications : Chem Comm·Kayoko HataYasuyuki Kita
Jun 10, 2005·Nature·Jaap E Klijn, Jan B F N Engberts
Oct 8, 2005·Organic Letters·Yannick BonvinAnthony G M Barrett
Nov 5, 2005·Organic Letters·Arthur J CatinoMichael P Doyle
Dec 21, 2005·Chemical Society Reviews·Chao-Jun Li, Liang Chen
Jun 17, 2006·The Journal of Organic Chemistry·Tanveer Mahammad Ali ShaikhArumugam Sudalai

❮ Previous
Next ❯

Citations

Oct 3, 2009·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Toshifumi Dohi
Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Sep 29, 2011·Angewandte Chemie·Caren RöbenKilian Muñiz
Jan 27, 2012·Chemistry : a European Journal·Anton Lishchynskyi, Kilian Muñiz
Mar 3, 2012·Chemistry, an Asian Journal·José A SoutoKilian Muñiz
Jun 22, 2017·Accounts of Chemical Research·Xi Wang, Armido Studer
Nov 21, 2014·Organic & Biomolecular Chemistry·Wei Jie Ang, Yulin Lam
Feb 28, 2015·Chemical Communications : Chem Comm·Yi WangYuanhua Wang
Aug 6, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Yuancheng LiAnne E V Gorden
Apr 2, 2019·Beilstein Journal of Organic Chemistry·Kelsey B LaMartinaNicholas C Boaz
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Toshifumi DohiYasuyuki Kita
Feb 6, 2020·Chemistry, an Asian Journal·Ankita BalPrasenjit Mal
Mar 16, 2013·Chemistry : a European Journal·Li MengZhiyong Wang
Aug 1, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yasuyuki Kita, Toshifumi Dohi
Oct 6, 2017·Organic Letters·Jie LiuYan-Biao Kang
Nov 19, 2013·The Journal of Organic Chemistry·Jian-Ping LiHai-Ming Guo
Nov 30, 2012·Organic Letters·Hisaaki ZaimokuHiroyuki Ishibashi
Nov 23, 2010·The Journal of Organic Chemistry·Wei Ren, Motoki Yamane
Jan 21, 2020·ACS Omega·Hasil AmanGary Jing Chuang
May 9, 2012·The Journal of Organic Chemistry·Yuancheng LiAnne E V Gorden
Sep 3, 2014·The Journal of Organic Chemistry·Qing JiangCancheng Guo

❮ 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.